SYN-S(N)2' PATHWAY IN THE REACTION OF CERTAIN GAMMA-(MESYLOXY) ALPHA, BETA-ENOATES WITH RCU(CN)MGX.BF3 REAGENTS - IMPORTANCE OF MGX AND BULKY R-GROUP UPON THE DIASTEREOSELECTIVITY

被引:47
作者
IBUKA, T [1 ]
TAGA, T [1 ]
HABASHITA, H [1 ]
NAKAI, K [1 ]
TAMAMURA, H [1 ]
FUJII, N [1 ]
CHOUNAN, Y [1 ]
NEMOTO, H [1 ]
YAMAMOTO, Y [1 ]
机构
[1] TOHOKU UNIV,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN
关键词
D O I
10.1021/jo00057a038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of protected serine- and threonine-derived gamma-(mesyloxy) alpha,beta-unsaturated esters with various magnesio organocyanocopper Lewis acid complexes have been investigated. The formation of syn-S(N)2' products, in addition to the normally expected anti-S(N)2' products, is taken as an indication that the reaction proceeds by a mechanism involving coordination of the magnesiocuprate with the C(delta)-N:C(gamma)-O syn-gamma-(mesyloxy) alpha,beta-enoates.
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页码:1207 / 1214
页数:8
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