Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction

被引:104
作者
Corey, EJ
Helal, CJ
机构
[1] Department of Chemistry, Harvard University, Cambridge
基金
美国国家科学基金会;
关键词
D O I
10.1016/0040-4039(96)01198-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new process has been developed for the highly enantioselective catalytic reduction of 2-aroylpyridines and successfully applied to the synthesis of (S)-carbinoxamine (1), a therapeutically important histamine H-1 antagonist. Related enantioselective reductions of 4-aroylpyridines and ortho-substituted benzophenones are also described. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5675 / 5678
页数:4
相关论文
共 38 条
[1]  
BARNHART ER, 1990, PHYSICIANS DESK REFE, P1898
[2]  
BAROUH V, 1971, J MED CHEM, V14, P834
[3]  
BOJADZIEV SE, 1987, B CHEM SOC JPN, V60, P2651
[4]  
BRAKER W, 1962, Patent No. 905993
[5]   PREPARATIVE SYNTHESES OF OPTICALLY PURE ORTHOSUBSTITUTED BENZHYDROLS BY ASYMMETRIC REDUCTIONS OF THE CORRESPONDING BENZOPHENONES [J].
BROWN, E ;
LEZE, A ;
TOUET, J .
TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :841-844
[6]   A SHORT AND EFFICIENT ENANTIOSELECTIVE ROUTE TO A KEY INTERMEDIATE FOR THE TOTAL SYNTHESIS OF FORSKOLIN [J].
COREY, EJ ;
JARDINE, PD .
TETRAHEDRON LETTERS, 1989, 30 (52) :7297-7300
[7]   1-MESITYL-2,2,2-TRIFLUOROETHANOL, AN OUTSTANDING NEW CHIRAL CONTROLLER FOR CATALYZED DIELS-ALDER REACTIONS [J].
COREY, EJ ;
CHENG, XM ;
CIMPRICH, KA .
TETRAHEDRON LETTERS, 1991, 32 (47) :6839-6842
[8]   CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF (3S)-2,3-OXIDOSQUALENE [J].
COREY, EJ ;
YI, KY ;
MATSUDA, SPT .
TETRAHEDRON LETTERS, 1992, 33 (17) :2319-2322
[9]   A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF CHIRAL MONOSUBSTITUTED OXIRANES [J].
COREY, EJ ;
HELAL, CJ .
TETRAHEDRON LETTERS, 1993, 34 (33) :5227-5230
[10]   DUAL BINDING MODES TO THE RECEPTOR FOR PLATELET ACTIVATING FACTOR (PAF) OF ANTI-PAF TRANS-2,5-DIARYLFURANS [J].
COREY, EJ ;
CHEN, CP ;
PARRY, MJ .
TETRAHEDRON LETTERS, 1988, 29 (24) :2899-2902