Bifunctional N‐Heterocylic Carbene‐Catalyzed Highly Enantioselective Trans‐Cyclopentannulation of Enals and Enones via Homoenolate | Zendy

Jiang Zhiwei | Zendy; Toffano Martial | Zendy; VoThanh Giang | Zendy; Bournaud Chloée | Zendy

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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).

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