Asymmetric borane reduction of prochiral ketones using aluminum triethoxide and chiral amino alcohols

被引：8

作者：

Yanagi, T ^{[1
]}

Kikuchi, K ^{[1
]}

Takeuchi, H ^{[1
]}

Ishikawa, T ^{[1
]}

Nishimura, T ^{[1
]}

Kamijo, T ^{[1
]}

机构：

[1] Kissei Pharmaceut Co Ltd, Cent Res Labs, Nagano 3998304, Japan

来源：

CHEMISTRY LETTERS | 1999年 / 11期

关键词：

D O I：

10.1246/cl.1999.1203

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric borane reduction of prochiral ketones with catalysts prepared in situ from aluminum triethoxide and chiral amino alcohols was examined, and the corresponding chiral alcohols were obtained in high optical purity.

引用

页码：1203 / 1204

页数：2

共 11 条

[1] AMINOBICYCLO2,2,1!HEPTANES .2. DIASTEREOISOMERIC DIMETHYLAMINOBORNYL ACETATES [J].

CHITTENDEN, RA ;

COOPER, GH .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (01) :49-+

[2] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[3]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

[4]

2-Z

[5] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[6] ASYMMETRIC REDUCTION OF AROMATIC KETONES WITH THE REAGENT PREPARED FROM (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL AND BORANE [J].

ITSUNO, S ;

ITO, K ;

HIRAO, A ;

NAKAHAMA, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (08) :469-470

[7]

Masui M, 1997, SYNLETT, P273

[8] A PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF ALPHA,ALPHA-DIARYL-2-PYRROLIDINEMETHANOL - PREPARATION AND CHEMISTRY OF THE CORRESPONDING OXAZABOROLIDINES [J].

MATHRE, DJ ;

JONES, TK ;

XAVIER, LC ;

BLACKLOCK, TJ ;

REAMER, RA ;

MOHAN, JJ ;

JONES, ETT ;

HOOGSTEEN, K ;

BAUM, MW ;

GRABOWSKI, EJJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :751-762

[9]

QUALLICH GJ, 1994, Patent No. 26751

[10] ASYMMETRIC-SYNTHESIS OF (R)-(-)-MUSCONE AND (S)-(+)-MUSCONE BY ENANTIOSELECTIVE CONJUGATE ADDITION OF CHIRAL DIMETHYLCUPRATE TO (E)-CYCLOPENTADEC-2-EN-1-ONE [J].

TANAKA, K ;

USHIO, H ;

KAWABATA, Y ;

SUZUKI, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1445-1452

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