A Lewis Acid-Catalyzed Diastereoselective Synthesis of Functionalized 2-Diazo-1,5-dicarbonyl Compounds

被引：10

作者：

Howard, Evan M. ^{[1
]}

Brewer, Matthias ^{[1
]}

机构：

[1] Univ Vermont, Dept Chem, Burlington, VT 05405 USA

来源：

ACS CATALYSIS | 2021年 / 11卷 / 19期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

conjugate addition; vinyl diazonium; diastereoselective; vinyl cation; 1,4-addition; Mukaiyama-Michael; furan; cation; FRAGMENTATION; ALKENEDIAZONIUM; CRYSTAL; ACETALS; KETONES; SALTS;

D O I：

10.1021/acscatal.1c03036

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A diverse array of 2-diazo-1,5-dicarbonyl compounds were formed by the Lewis acid-catalyzed reaction of enoxysilanes with beta-hydroxy-alpha-diazo carbonyls. This reaction proceeds via the Zn(OTf)(2)-catalyzed dehydroxylation of the beta-hydroxy-alpha-diazo carbonyl to form a vinyl diazonium ion intermediate that is intercepted by the enoxysilane nucleophile to give diazo-containing scaffolds with increased molecular complexity. The reaction appears to be general, and a variety of functional groups, including common protecting groups, are well tolerated. The 2-diazo-1,5-dicarbonyl products are formed in yields of up to 99% with diastereoselectivity up to >20:1.

引用

页码：12203 / 12207

页数：5

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