CONJUGATE-ADDITION REACTIONS OF ALPHA-SULFINYL KETIMINE ANIONS WITH A METHYL ALPHA-AMIDOACRYLATE - CONCISE ASYMMETRIC TOTAL SYNTHESES OF (-)-SLAFRAMINE AND (-)-6-EPISLAFRAMINE

被引：48

作者：

HUA, DH

PARK, JG

KATSUHIRA, T

BHARATHI, SN

机构：

[1] Department of Chemistry, Kansas State University, Manhattan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 08期

关键词：

D O I：

10.1021/jo00060a034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The in-situ 1,4-addition/ring-closure reactions of chiral alpha-sulfinyl ketimine anions with a methyl alpha-amidoacrylate provide a simple method for the construction of optically pure 6-aminoindolizidinones. This method afforded the syntheses of (-)-slaframine and (-)-6-epislaframine in six steps, respectively, from (+/-)-3-[(tert-butyldimethylsilyl)oxy]-4,5-dihydro-2-methyl-3H-pyrrole (9). Stereoselective reductions of alpha-sulfinyl ketimines (such as 10) were also developed.

引用

页码：2144 / 2150

页数：7

共 27 条

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