Asymmetric synthesis of 2H-Azirine 2-carboxylate esters

被引：57

作者：

Davis, FA ^{[1
]}

Liu, H ^{[1
]}

Liang, CH ^{[1
]}

Reddy, GV ^{[1
]}

Zhang, YL ^{[1
]}

Fang, TN ^{[1
]}

Titus, DD ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 24期

关键词：

D O I：

10.1021/jo991389f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2H-Azirine 2-carboxylate esters (5), the smallest unsaturated nitrogen heterocycle, are readily prepared in enantiomerically pure form via the base-induced elimination of sulfenic acid (RSOH) from nonracemic N-sulfinylaziridine 2-carboxylate esters (4). Optimum yields were obtained when the aziridine was treated with TMSCl at -95 degrees C followed by LDA, which was attributed to the improved leaving group ability of an silicon-oxonium species. By using this new methodology the first asymmetric syntheses of the marine cytotoxic antibiotics (R)-(-)- and (S)-(+)-dysidazirine (2) were accomplished.

引用

页码：8929 / 8935

页数：7

共 46 条

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