Premium
Synthesis of Functionalized α‐Vinyl Aldehydes from Enaminones
Author(s) -
Chen Jie,
Guo Pan,
Zhang Jianguo,
Rong Jiaxin,
Sun Wangbin,
Jiang Yaojia,
Loh TeckPeng
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201906213
Subject(s) - cyclopropanation , cyclopropane , aldehyde , stereoselectivity , chemistry , cleavage (geology) , substrate (aquarium) , bond cleavage , selectivity , catalysis , combinatorial chemistry , organic chemistry , materials science , ring (chemistry) , oceanography , fracture (geology) , composite material , geology
An efficient Rh II ‐catalyzed synthesis of functionalized α‐vinyl aldehydes with high E / Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C−C bond cleavage of the cyclopropane intermediates leads to formation of α‐vinyl aldehyde derivatives with high E / Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.