ENANTIOSELECTIVE CATALYTIC BORANE REDUCTIONS OF ACHIRAL KETONES - SYNTHESIS AND APPLICATION OF NEW CATALYSTS PREPARED FROM (S)-TERT-LEUCINE AND (S)-AZETIDINECARBOXYLIC ACID

被引：38

作者：

BEHNEN, W ^{[1
]}

DAUELSBERG, C ^{[1
]}

WALLBAUM, S ^{[1
]}

MARTENS, J ^{[1
]}

机构：

[1] UNIV OLDENBURG,FACHBEREICH CHEM,AMMERLANDER HEERSTR 114-118,W-2900 OLDENBURG,GERMANY

来源：

SYNTHETIC COMMUNICATIONS | 1992年 / 22卷 / 15期

关键词：

D O I：

10.1080/00397919208019066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiocontrolled reduction of prochiral ketones with borane in the presence of homochiral amino alcohols 1 - 3 as enantioselective catalysts afforded the corresponding secondary alcohols in moderate to high (69 to >99 %) optical yields.

引用

页码：2143 / 2153

页数：11

共 36 条

[1] ASYMMETRIC INDUCTION AND CONFIGURATIONAL CORRELATIONS IN OXIDATIONS AT SULPHUR .V. OXIDATIONS OF OPTICALLY ACTIVE ESTERS OF O-(METHYLTHIO)BENZOIC ACID BY ACHIRAL PEROXY-ACIDS
BARBIERI, G
DAVOLI, V
MORETTI, I
MONTANARI, F
TORRE, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (05): : 731 - +
[2] ENANTIOSELECTIVE SYNTHESIS USING CHIRAL HETEROGENEOUS CATALYSTS
BLASER, HU
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (09) : 843 - 866
[3] The resolution of beta-naphthylmethylcarbinol
Collyer, TA
Kenyon, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1940, : 676 - 679
[4] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE
COREY, EJ
SHIBATA, S
BAKSHI, RK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) : 2861 - 2863
[5] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS
COREY, EJ
BAKSHI, RK
SHIBATA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5551 - 5553
[6] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES
COREY, EJ
BAKSHI, RK
SHIBATA, S
CHEN, CP
SINGH, VK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) : 7925 - 7926
[7] NEW ENANTIOSELECTIVE ROUTES TO BIOLOGICALLY INTERESTING COMPOUNDS
COREY, EJ
[J]. PURE AND APPLIED CHEMISTRY, 1990, 62 (07) : 1209 - 1216
[8] Downes R.A., 1982, PASP, V94, P590
[9] INDUCTION OF ASYMMETRY BY AMINO-ACIDS
DRAUZ, K
KLEEMAN, A
MARTENS, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (08): : 584 - 608
[10] HASHIMOTO S, 1978, TETRAHEDRON LETT, P573

← 1 2 3 4 →