METAL-AMIDES IN ORGANIC-SYNTHESIS .7. STEREODIVERGENT SYNTHESIS OF THE ENOLATES OF A BETA-AMINO ESTER BY USING LITHIUM N-BENZYLTRIMETHYLSILYLAMIDE

被引：80

作者：

ASAO, N ^{[1
]}

UYEHARA, T ^{[1
]}

YAMAMOTO, Y ^{[1
]}

机构：

[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

TETRAHEDRON | 1990年 / 46卷 / 13-14期

关键词：

D O I：

10.1016/S0040-4020(01)85581-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereoselective generation of both Z- and E-enolates (1 and 3)2 is accomplished by the conjugate addition of lithium N-benzyltrimethylsilylamide (LSA) to methyl crotonate. The alkylation with alkyl halides and aldol condensation with aldehydes via 1 and 3 are studied. The alkylation of 3 produces moderate to good syn selectivity, while that of 1 gives no selectivity. The aldol condensation of 1 affords the anti-syn isomer (11) predominantly, whereas that of 3 gives the syn-anti isomer (14) preferentially. © 1990.

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页码：4563 / 4572

页数：10

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