Premium
Bifunctional N‐Heterocylic Carbene‐Catalyzed Highly Enantioselective Trans‐Cyclopentannulation of Enals and Enones via Homoenolate
Author(s) -
Jiang Zhiwei,
Toffano Martial,
VoThanh Giang,
Bournaud Chloée
Publication year - 2021
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202001513
Subject(s) - bifunctional , enantioselective synthesis , catalysis , carbene , yield (engineering) , chemistry , thio , combinatorial chemistry , organocatalysis , hydrogen bond , organic chemistry , materials science , molecule , metallurgy
An efficient and flexible synthesis of a new class of chiral bifunctional NHC catalyst has been reported. These new imidazolylidene NHCs, bearing a (thio)urea function as a hydrogen bond donor promoted efficiently highly diastereoselective trans ‐cyclopentannulation of enals and enones in moderate to good yields (up to 69 % yield) along with excellent enantioselectivity (up to 96 % ee). This methodology could be applied to a large variety of substrates (30 examples).