Multicomponent reactions .2. Stereoselective synthesis of 1(S)-camphor-2-cis-methylidene-isocyanide and its application in Passerini- and Ugi-reaction

被引：42

作者：

Bock, H ^{[1
]}

Ugi, I ^{[1
]}

机构：

[1] TECH UNIV MUNICH,INST ORGAN CHEM & BIOCHEM,D-85747 GARCHING,GERMANY

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1997年 / 339卷 / 04期

关键词：

D O I：

10.1002/prac.19973390167

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The use of unsaturated isocyanides in multicomponent reactions leads to N-vinylamides, which can be cleaved to carboxylic acids or esters under mild conditions. The chiral 1 (S)-camphor-2-cis-methylidene-isocyanide (5) can be prepared in two steps from camphor and methylisocyanide. Its application in the Passerini reaction generates alpha-acyloxyamides (6, 7, 8, 9) with a diastereomeric excess of > 92%, in the Ugi reaction alpha-acylaminoamides with a diastereomeric excess of 0% are formed.

引用

页码：385 / 389

页数：5

共 19 条

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