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Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C 3 ‐Chirogenic Center
Author(s) -
Liu Chong,
Yuan Jing,
Zhang Zhenfeng,
Gridnev Ilya D.,
Zhang Wanbin
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202017190
Subject(s) - hydroacylation , alkene , isomerization , intramolecular force , enantioselective synthesis , chemistry , catalysis , stereochemistry , organic chemistry , aldehyde
A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five‐membered rhodacycle intermediate, 3‐enals were converted to C 3 ‐ or C 3 ,C 5 ‐chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.