NL8201656A - Chirale fosfienen, alsmede werkwijzen ter bereiding van dergelijke fosfienen. - Google Patents

Chirale fosfienen, alsmede werkwijzen ter bereiding van dergelijke fosfienen. Download PDF

Info

Publication number: NL8201656A
Authority: NL; Netherlands
Prior art keywords: formula; phosphino; compound; phosphine; diphenyl
Prior art date: 1981-04-22

Application number

NL8201656A

Other languages

English (en)

Dutch (nl)

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-04-22

Filing date

1982-04-21

Publication date

1982-11-16

1982-04-21 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1982-11-16 Publication of NL8201656A publication Critical patent/NL8201656A/nl

Links

238000000034 method Methods 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims description 73
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 29
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 28
229910052703 rhodium Inorganic materials 0.000 claims description 28
239000010948 rhodium Substances 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 28
239000003054 catalyst Substances 0.000 claims description 24
FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 15
239000004305 biphenyl Substances 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
150000003003 phosphines Chemical class 0.000 claims description 10
235000010290 biphenyl Nutrition 0.000 claims description 9
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 9
125000006267 biphenyl group Chemical group 0.000 claims description 8
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 3
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 2
RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 claims 1
101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 claims 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
101150068774 thyX gene Proteins 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
229910052786 argon Inorganic materials 0.000 description 24
238000005984 hydrogenation reaction Methods 0.000 description 22
239000000203 mixture Substances 0.000 description 19
239000000047 product Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
238000004821 distillation Methods 0.000 description 12
239000010410 layer Substances 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
-1 methoxy, ethoxy, isopropoxy, n-butoxy Chemical group 0.000 description 11
239000013078 crystal Substances 0.000 description 10
229940115458 pantolactone Drugs 0.000 description 10
SIEVQTNTRMBCHO-UHFFFAOYSA-N pantolactone Natural products CC1(C)OC(=O)CC1O SIEVQTNTRMBCHO-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000012043 crude product Substances 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
229910052744 lithium Inorganic materials 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000012429 reaction media Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
SERHXTVXHNVDKA-UHFFFAOYSA-N pantolactone Chemical compound CC1(C)COC(=O)C1O SERHXTVXHNVDKA-UHFFFAOYSA-N 0.000 description 5
150000003283 rhodium Chemical class 0.000 description 5
239000012267 brine Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000004210 ether based solvent Substances 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
229910001220 stainless steel Inorganic materials 0.000 description 4
239000010935 stainless steel Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
RRSCGNXXNRAXJC-UHFFFAOYSA-N bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1PC1=CC=C(C)C=C1 RRSCGNXXNRAXJC-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
150000002642 lithium compounds Chemical class 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
239000002243 precursor Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000012485 toluene extract Substances 0.000 description 3
ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 3
239000005052 trichlorosilane Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
QADGMTMQPJGHQE-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]phosphanyl-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1PC1=CC=C(N(C)C)C=C1 QADGMTMQPJGHQE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000011914 asymmetric synthesis Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
FWKICRREDMVWRF-UHFFFAOYSA-N bis(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1PC1=CC=C(OC)C=C1 FWKICRREDMVWRF-UHFFFAOYSA-N 0.000 description 2
HILVSVQPQFWLAA-UHFFFAOYSA-N bis[4-(dimethylamino)phenyl]-oxophosphanium Chemical compound C1=CC(N(C)C)=CC=C1[P+](=O)C1=CC=C(N(C)C)C=C1 HILVSVQPQFWLAA-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 2
PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
XYZWMVYYUIMRIZ-UHFFFAOYSA-N 4-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(Br)C=C1 XYZWMVYYUIMRIZ-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
239000004913 cyclooctene Substances 0.000 description 1
UZEFVQBWJSFOFE-UHFFFAOYSA-N dibutyl hydrogen phosphite Chemical compound CCCCOP(O)OCCCC UZEFVQBWJSFOFE-UHFFFAOYSA-N 0.000 description 1
BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical group P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000010791 quenching Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010405 reoxidation reaction Methods 0.000 description 1
MMRXYMKDBFSWJR-UHFFFAOYSA-K rhodium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Rh+3] MMRXYMKDBFSWJR-UHFFFAOYSA-K 0.000 description 1
YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
WMUVAMXULTVKIW-UHFFFAOYSA-K tribromorhodium;hydrate Chemical compound O.Br[Rh](Br)Br WMUVAMXULTVKIW-UHFFFAOYSA-K 0.000 description 1
HSSMNYDDDSNUKH-UHFFFAOYSA-K trichlororhodium;hydrate Chemical compound O.Cl[Rh](Cl)Cl HSSMNYDDDSNUKH-UHFFFAOYSA-K 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8201656A 1981-04-22 1982-04-21 Chirale fosfienen, alsmede werkwijzen ter bereiding van dergelijke fosfienen. NL8201656A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US25637881		1981-04-22
US06/256,378 US4343741A (en)	1981-04-22	1981-04-22	Chiral phosphines

Publications (1)

Publication Number	Publication Date
NL8201656A true NL8201656A (nl)	1982-11-16

Family

ID=22972026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8201656A NL8201656A (nl)	1981-04-22	1982-04-21	Chirale fosfienen, alsmede werkwijzen ter bereiding van dergelijke fosfienen.

Country Status (9)

Country	Link
US (1)	US4343741A (de)
JP (1)	JPS57181093A (de)
BE (1)	BE892915A (de)
CH (1)	CH650263A5 (de)
DE (1)	DE3214828A1 (de)
FR (1)	FR2504534B1 (de)
GB (1)	GB2097003B (de)
IT (1)	IT1212523B (de)
NL (1)	NL8201656A (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4539411A (en) *	1982-02-05	1985-09-03	Hoffmann-La Roche Inc.	Rhodium complexes of chiral phosphines
FR2558471B1 (fr) *	1984-01-19	1987-11-20	Isochem Sa	Procede de preparation d'aspartyl peptides, et nouveaux intermediaires de synthese
DE3403194A1 (de) *	1984-01-31	1985-08-01	Degussa Ag, 6000 Frankfurt	Optisch aktive 3,4-bis-(diphenylphosphino)-pyrrolidine, diese als chirale liganden enthaltende rhodiumkomplexe und deren verwendung
EP0158875B1 (de) *	1984-04-19	1989-12-13	F. Hoffmann-La Roche Ag	Chirale Rhodium-diphosphinkomplexe für asymmetrische Hydrierungen
ATE77383T1 (de) *	1985-10-18	1992-07-15	Hoffmann La Roche	Chirale rhodium-diphosphinkomplexe fuer asymmetrische hydrierungen.
EP0251164B1 (de) *	1986-06-25	1992-12-16	Kazuo Achiwa	Chirale Phosphinopyrrolidin-Verbindungen und ihre Verwendung für asymetrische Synthese optisch aktiver Verbindungen
EP0290075A3 (de) *	1987-05-08	1989-02-22	Shell Internationale Researchmaatschappij B.V.	Diaryl Phosphyde
JP2816555B2 (ja) *	1988-03-07	1998-10-27	富士薬品工業株式会社	新規なホスフイノピロリジン化合物およびそれを用いる不斉合成法
DE4001019A1 (de) *	1990-01-16	1991-07-18	Degussa	Verfahren zur asymmetrischen hydrierung von (alpha)-ketocarbonylverbindungen zu optisch aktiven (alpha)-hydroxycarbonylverbindungen
FR2693190B1 (fr) *	1992-07-02	1994-09-23	Elf Aquitaine	Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO.
AU5191898A (en) *	1996-11-29	1998-06-22	Fuji Yakuhin Kogyo Kabushiki Kaisha	Novel phosphinopyrrolidine compounds and process for producing the same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3883580A (en) *	1972-02-09	1975-05-13	Monsanto Co	Asymmetric reduction of ketones to form optically active alcohols
US4008281A (en) *	1973-12-03	1977-02-15	Monsanto Company	Asymmetric catalysis
DE2411440B2 (de) *	1974-03-11	1977-12-15	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von methacrylsaeure und butyrolacton
US4123465A (en) *	1975-10-16	1978-10-31	Hoffmann-La Roche Inc.	Chiral tertiary phosphines
JPS53105421A (en) *	1977-02-28	1978-09-13	Sagami Chem Res Center	Preparation of optical active alpha-hydroxycarboxylic acid esters acid esters

1981
- 1981-04-22 US US06/256,378 patent/US4343741A/en not_active Expired - Fee Related
1982
- 1982-03-26 CH CH1882/82A patent/CH650263A5/de not_active IP Right Cessation
- 1982-04-20 FR FR8206739A patent/FR2504534B1/fr not_active Expired
- 1982-04-20 IT IT8220831A patent/IT1212523B/it active
- 1982-04-21 GB GB8211580A patent/GB2097003B/en not_active Expired
- 1982-04-21 JP JP57065545A patent/JPS57181093A/ja active Pending
- 1982-04-21 NL NL8201656A patent/NL8201656A/nl not_active Application Discontinuation
- 1982-04-21 DE DE19823214828 patent/DE3214828A1/de not_active Withdrawn
- 1982-04-21 BE BE0/207882A patent/BE892915A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH650263A5 (de)	1985-07-15
DE3214828A1 (de)	1982-11-11
FR2504534B1 (fr)	1986-04-18
BE892915A (fr)	1982-10-21
FR2504534A1 (fr)	1982-10-29
IT1212523B (it)	1989-11-30
GB2097003B (en)	1984-08-15
JPS57181093A (en)	1982-11-08
GB2097003A (en)	1982-10-27
IT8220831A0 (it)	1982-04-20
US4343741A (en)	1982-08-10

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1988-12-01	BV	The patent application has lapsed

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