Asymmetric synthesis of 4,4-disubstituted-2-cyclohexen-1-ones from a chiral 2-(trimethylsilyl)benzamide

被引:7
作者
Schultz, AG
Pettus, L
机构
[1] Department of Chemistry, Rensselaer Polytechnic Institute, Troy
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(97)01215-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Birch reduction-alkylation of the chiral 2-(trimethylsilyl)benzamide 4 provides 1,4-cyclohexadienes 5b-5e with diastereomer ratios of >100:1. The conversions of 5b-5e to the 4,4-disubstituted-2-cyclohexen-1-ones 8b-8e are described. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5433 / 5436
页数:4
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共 15 条
[11]   Asymmetric total synthesis of (+)-apovincamine and a formal synthesis of (+)-vincamine. Demonstration of a practical ''asymmetric linkage'' between aromatic carboxylic acids and chiral acyclic substrates [J].
Schultz, AG ;
Malachowski, WP ;
Pan, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1223-1229
[12]   PROGRESS IN THE DEVELOPMENT OF METHODS FOR ASYMMETRIC ORGANIC-SYNTHESIS [J].
SCHULTZ, AG .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1994, 41 (05) :487-495
[13]   AN IMPROVED PROCEDURE FOR THE CONVERSION OF 3,3-DISUBSTITUTED-1,4-CYCLOHEXADIENES TO 2,5-CYCLOHEXADIEN-1-ONES [J].
SCHULTZ, AG ;
TAVERAS, AG ;
HARRINGTON, RE .
TETRAHEDRON LETTERS, 1988, 29 (32) :3907-3910
[14]   SOLID-STATE PHOTOCHEMISTRY - REMARKABLE EFFECTS OF THE PACKING OF MOLECULES IN CRYSTALS ON THE DIASTEREOSELECTIVITY OF THE INTRAMOLECULAR 2+2 PHOTOCYCLOADDITION OF A 4-(3'-BUTENYL)-2,5-CYCLOHEXADIEN-1-ONE [J].
SCHULTZ, AG ;
TAVERAS, AG ;
TAYLOR, RE ;
THAM, FS ;
KULLNIG, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) :8725-8727
[15]   ASYMMETRIC SYNTHESES OF 1,6-DIALKYL-1,4-CYCLOHEXADIENE DERIVATIVES [J].
SCHULTZ, AG ;
GREEN, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :4931-4936