Syntheses of optically active trifluoronorcoronamic acids

被引：37

作者：

Katagiri, T ^{[1
]}

Irie, M ^{[1
]}

Uneyama, K ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 16期

关键词：

D O I：

10.1021/ol0059955

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Syntheses of optically active trifluoronorcoronamic acid 6 and its diastereomer 9 are described. Highly stereospecific and diastereoselective S(N)2 cyclization of gamma-cyanohydrins 3a and 3b gave cydopropyl nitriles 4a and 4b. Hydrolysis of the cyano group and deprotection of the amino group of 4a provide trifluoronorcoronamic acid 6, Hofmann rearrangement of the amide which was generated by hydrolysis of the cyano group and oxidative cleavage of the aryl ring of 4b to provide trifluoro-allo-norcoronamic acid 9.

引用

页码：2423 / 2425

页数：3

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