JPS6468A - Tertiary amino-alcohol compound and production of optically active secondary alcohol using said compound - Google Patents
Tertiary amino-alcohol compound and production of optically active secondary alcohol using said compoundInfo
- Publication number
- JPS6468A JPS6468A JP10103287A JP10103287A JPS6468A JP S6468 A JPS6468 A JP S6468A JP 10103287 A JP10103287 A JP 10103287A JP 10103287 A JP10103287 A JP 10103287A JP S6468 A JPS6468 A JP S6468A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- optically active
- alcohol
- alkyl
- active secondary
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 150000003333 secondary alcohols Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 2
- -1 amino-alcohol compound Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910020101 MgC2 Inorganic materials 0.000 abstract 1
- XIJAGFLYYNXCAB-KRWDZBQOSA-N [(2s)-1-methylpyrrolidin-2-yl]-diphenylmethanol Chemical compound CN1CCC[C@H]1C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 XIJAGFLYYNXCAB-KRWDZBQOSA-N 0.000 abstract 1
- 150000001414 amino alcohols Chemical group 0.000 abstract 1
- 238000007294 asymmetric addition reaction Methods 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Landscapes
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
PURPOSE: To obtain an optically active secondary alcohol in high yield and in high optical purity, by subjecting a dialkylzinc to asymmetric addition reaction to an aldehyde by using a specific tertiary amino-alcohol as a catalyst.
CONSTITUTION: A dialkylzinc is added to an aldehyde by using a compound shown by formula I [R4 is 1W6C alkyl; R5 and R6 are H or phenyl which may contain 1W5 substituent groups (halogen or NO2); Z is H, Li, Na, K or MgC2H5; *is optically active carbon] such as (S)-diphenyl(1-methylpyrrolidin-2-yl) methanol as a catalyst to give an optically active secondary alcohol shown by formula II [R1 is 1W12C alkyl; R2 is 1W12C alkyl or group shown by formula III (X and Y are Y, halogen, NO2 or CN; m and n are 0W2; α and β are single bond, COO, OOC, OCH2, OCH2O or O; R3 is 1W16C alkyl)]. The amount of the catalyst used is ≤5mol.% based on the aldehyde and that of the dialkylzinc is 1W2.5 equivalents.
COPYRIGHT: (C)1989,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10103287A JPS6468A (en) | 1987-02-27 | 1987-04-23 | Tertiary amino-alcohol compound and production of optically active secondary alcohol using said compound |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62-44318 | 1987-02-27 | ||
| JP4431887 | 1987-02-27 | ||
| JP10103287A JPS6468A (en) | 1987-02-27 | 1987-04-23 | Tertiary amino-alcohol compound and production of optically active secondary alcohol using said compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0168A JPH0168A (en) | 1989-01-05 |
| JPS6468A true JPS6468A (en) | 1989-01-05 |
Family
ID=26384172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10103287A Pending JPS6468A (en) | 1987-02-27 | 1987-04-23 | Tertiary amino-alcohol compound and production of optically active secondary alcohol using said compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6468A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4778733A (en) * | 1986-07-03 | 1988-10-18 | Engelhard Corporation | Low toxicity corrosion resistant solder |
| JPH01313445A (en) * | 1988-06-13 | 1989-12-18 | Toyo Stauffer Chem Co | Method for catalytic asymmetric and amplifying synthesis of secondary alcohol having high level of optical purity |
-
1987
- 1987-04-23 JP JP10103287A patent/JPS6468A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4778733A (en) * | 1986-07-03 | 1988-10-18 | Engelhard Corporation | Low toxicity corrosion resistant solder |
| JPH01313445A (en) * | 1988-06-13 | 1989-12-18 | Toyo Stauffer Chem Co | Method for catalytic asymmetric and amplifying synthesis of secondary alcohol having high level of optical purity |
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