Superelectrophilic Fe(III)-Ion Pairs as Stronger Lewis Acid Catalysts for (E)-Selective Intermolecular Carbonyl-Olefin Metathesis

被引：21
|
作者：
Albright, Haley [1 ]
Vonesh, Hannah L. [1 ]
Schindler, Corinna S. [1 ]
机构：
[1] Univ Michigan, Willard Henry Dow Lab, Dept Chem, Ann Arbor, MI 48109 USA
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 08期
基金：
美国国家科学基金会;
关键词：
PHOTOPROTOLYTIC OXAMETATHESIS; CYCLOADDITIONS; ALDEHYDES;
D O I：
10.1021/acs.orglett.0c00917
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An intermolecular carbonyl-olefin metathesis reaction is described that relies on superelectrophilic Fe(III)-based ion pairs as stronger Lewis acid catalysts. This new catalytic system enables selective access to (E)-olefins as carbonyl-olefin metathesis products. Mechanistic investigations suggest the regioselective formation and stereospecific fragmentation of intermediate oxetanes to be the origin of this selectivity. The optimized conditions are general for a variety of aryl aldehydes and trisubstituted olefins and are demonstrated for 28 examples in up to 64% overall yield.
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收藏
页码：3155 / 3160
页数：6
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