ASYMMETRIC-SYNTHESIS VIA ELECTROPHILE-MEDIATED CYCLIZATIONS

被引:61
作者
FOX, DNA
GALLAGHER, T
机构
[1] School of Chemistry, Bath University, Bath, Avon
关键词
D O I
10.1016/S0040-4020(01)85590-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The electrophile-mediated cyclisation of a series of allenic amines (8a-e), carrying a chiral benzylic residue on nitrogen, has been examined using Ag(I) and Pd(II). The cyclised products, (9/10)(using Ag(I)) and (12/13)(using Pd(II), CO, MeOH), are formed diastereoselectively. With Ag(I) up to 81% d.e. has been observed and the stereochemical course of this reaction has been established. The Pd(II)-mediated cyclisation is less selective (up to 43% d.e.) and the factors controlling the selectivities of both of these reactions are discussed. © 1990.
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收藏
页码:4697 / 4710
页数:14
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