Enantioselective Synthesis of Skipped Dienes via Iridium-Catalyzed Allylic Alkylation of Phosphonates

被引：9
|
作者：
Seal, Arko [1 ]
Mukherjee, Santanu [1 ]
机构：
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, India
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 13期
关键词：
ALKENES; ALLYLATION; NUCLEOPHILE; AMINATION; DIASTEREO; EFFICIENT; ACETATES; LIGANDS;
D O I：
10.1021/acs.orglett.3c00505
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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 alpha-C(sp2)-H allylic alkylation of alpha,beta-unsaturated carbonyls and acrylonitrile.
引用
收藏
页码：2253 / 2257
页数：5
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