ASYMMETRIC SYNTHESES OF 1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID-DERIVATIVES

被引：111

作者：

WILLIAMS, RM

FEGLEY, GJ

机构：

[1] Department of Chemistry, Colorado State University, Fort Collins

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 23期

关键词：

D O I：

10.1021/ja00023a030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active D-erythro-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (13) can be efficiently condensed with various aldehydes via the Emmons-Horner-Wadsworth procedure to provide alpha-beta-dehydrolactone adducts (14). It was found that the adducts (14) were smoothly cyclopropanated with the ylide of racemic [[(diethylamino)methyl]phenyl]oxosulfonium tetrafluoroborate to furnish in high chemical and optical yields the desired cyclopropanes (15). Final deblocking to the requisite amino acids was accomplished with dissolving-metal reduction. The syntheses of [H-2(2)]ACC, MeACC (norcoronamic acid), EtACC (coronamic acid), and BuACC are described.

引用

页码：8796 / 8806

页数：11

共 92 条

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