Rhodium-catalyzed 1,4-addition of alkenylzirconocene chlorides to electron deficient alkenes

被引：25
作者：
Kakuuchi, A [1 ]
Taguchi, T [1 ]
Hanzawa, Y [1 ]
机构：
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
来源：
TETRAHEDRON | 2004年 / 60卷 / 06期
关键词：
D O I：
10.1016/j.tet.2003.08.073
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 1,4-conjugated addition of alkenylzirconocene chloride complexes to alpha,beta-enones, alpha,beta-enoic acid esters, and alpha,beta-enoic acid amides can be efficiently achieved by the use of [RhCl(cod)](2) catalyst. A high diastereoselectivity (95% yield, 90% de) was obtained through the reaction of alpha,beta-enoic acid amide derived from Oppolzer's sultam and 2-butenoyl chloride, while the use of Evans' chiral oxazolidinone as a chiral auxiliary in place of Oppolzer's sultam, gave a poor diastereoselectivity (98% yield, 26% de). (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1293 / 1299
页数：7
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