对映选择合成
化学
立体中心
筑地反应
烯丙基重排
铱
烷基化
丙烯腈
催化作用
有机化学
组合化学
聚合物
共聚物
作者
Arko Seal,Santanu Mukherjee
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-03-26
卷期号:25 (13): 2253-2257
被引量:5
标识
DOI:10.1021/acs.orglett.3c00505
摘要
An enantioselective synthesis of skipped dienes has been developed based on an iridium-catalyzed allylic alkylation of phosphonates and Horner-Wadsworth-Emmons olefination. This two-step protocol uses easily accessible substrates and delivers C2-substituted skipped dienes bearing a C3 stereogenic center, generally with outstanding enantioselectivities (up to 99.5:0.5 er). This is the first catalytic enantioselective allylic alkylation of phosphonates, and the overall process represents a formal enantioselective α-C(sp2)-H allylic alkylation of α,β-unsaturated carbonyls and acrylonitrile.
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