Bifunctional N‐Heterocylic Carbene‐Catalyzed Highly Enantioselective Trans‐Cyclopentannulation of Enals and Enones via Homoenolate. Issue 2 (3rd December 2020)

• Record Type: Journal Article
• Authors: Jiang, Zhiwei; Toffano, Martial; Vo‐Thanh, Giang; Bournaud, Chloée
• Is Part Of: ChemCatChem. Volume 13:Issue 2(2021)
• Page Start: 712
• Page End: 717
• Publication Date: 2020-12-03
• Subjects: Asymmetric catalysis -- cyclopentannulation -- N-heterocyclic carbenes -- homoenolate -- organocatalysis; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.202001513
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: 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). Abstract : Asymmetric catalysis : New bifunctional chiral NHC catalysts were prepared and proved their efficiency to promote highly diastereoselective trans‐cyclopentannulation in moderate to good yields and excellent enantioselectivity.