ASYMMETRIC BORANE REDUCTION OF ACHIRAL KETONES MEDIATED BY A-CHIRAL OXAZABOROLIDINE DERIVED FROM (-)-EPHEDRINE

被引:13
作者
CHO, BT
CHUN, YS
机构
[1] Department of Chemistry, Hallym University, Chunchon
关键词
D O I
10.1016/S0957-4166(00)86055-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric borane reduction of achiral ketones in the presence of a chiral oxazaborolidine derived from (-)-ephedrine yielded the corresponding alcohols in optical yields of 41 - 83 % ee.
引用
收藏
页码:1539 / 1542
页数:4
相关论文
共 25 条
[1]   ENANTIOSELECTIVE CATALYTIC BORANE REDUCTIONS OF ACHIRAL KETONES - SYNTHESIS AND APPLICATION OF NEW CATALYSTS PREPARED FROM (S)-TERT-LEUCINE AND (S)-AZETIDINECARBOXYLIC ACID [J].
BEHNEN, W ;
DAUELSBERG, C ;
WALLBAUM, S ;
MARTENS, J .
SYNTHETIC COMMUNICATIONS, 1992, 22 (15) :2143-2153
[2]   NOVEL CONCEPTS IN DIRECTED BIARYL SYNTHESIS .12. 1ST ATROPO-ENANTIOSELECTIVE RING-OPENING OF ACHIRAL BIARYLS CONTAINING LACTONE BRIDGES WITH CHIRAL HYDRIDE-TRANSFER REAGENTS DERIVED FROM BORANE [J].
BRINGMANN, G ;
HARTUNG, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (06) :761-762
[3]   SELECTIVE REDUCTIONS .40. A CRITICAL-EXAMINATION OF THE RELATIVE EFFECTIVENESS OF VARIOUS REDUCING AGENTS FOR THE ASYMMETRIC REDUCTION OF DIFFERENT CLASSES OF KETONES [J].
BROWN, HC ;
PARK, WS ;
CHO, BT ;
RAMACHANDRAN, PV .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5406-5412
[4]  
CHO BT, 1992, TETRAHEDRON-ASYMMETR, V3, P73
[5]  
CHO BT, 1991, B KOR CHEM SOC, V12, P662
[6]  
CHO BT, 1990, J KOREAN CHEM SOC, V34, P313
[7]   A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS AND DEUTERATED PRIMARY ALCOHOLS BY CARBONYL REDUCTION [J].
COREY, EJ ;
LINK, JO .
TETRAHEDRON LETTERS, 1989, 30 (46) :6275-6278
[8]   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
[9]   A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S ;
CHEN, CP ;
SINGH, VK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926
[10]   (+)-1(S),5(R),8(S)-8-PHENYL-2-AZABICYCLO[3.3.0]OCTAN-8-OL N,O-METHYLBORONATE (2) AND ITS ENANTIOMER, CHIRAL CHEMZYMES WHICH SERVE AS CATALYSTS FOR THEIR OWN ENANTIOSELECTIVE SYNTHESIS [J].
COREY, EJ ;
CHEN, CP ;
REICHARD, GA .
TETRAHEDRON LETTERS, 1989, 30 (41) :5547-5550