Bifunctional N‐Heterocylic Carbene‐Catalyzed Highly Enantioselective Trans‐Cyclopentannulation of Enals and Enones via Homoenolate.
- Resource Type
- Article
- Authors
- Jiang, Zhiwei; Toffano, Martial; Vo‐Thanh, Giang; Bournaud, Chloée
- Source
- ChemCatChem. 1/20/2021, Vol. 13 Issue 2, p712-717. 6p.
- Subject
- *CARBONYL compounds
*HYDROGEN bonding
*CATALYSTS
*NITROALKENES
*UREA
*ORGANOCATALYSIS
- Language
- ISSN
- 1867-3880
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 FROM AUTHOR]