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
收藏
页码：12203 / 12207
页数：5
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