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Design, Synthesis, and Organocatalytic Activity of N‐Heterocyclic Carbenes Functionalized with Hydrogen‐Bond Donors in Enantioselective Reactions of Homoenolates

2013; Wiley; Volume: 2013; Issue: 36 Linguagem: Inglês

10.1002/ejoc.201301366

1434-193X

Faisal Nawaz, Mehdi Zaghouani, Damien Bonne, Olivier Chuzel, Jean Rodriguez, Yoann Coquerel,

Synthetic Organic Chemistry Methods

Abstract A focused library of chiral imidazolinium salts functionalized with urea‐type hydrogen‐bond donor moieties has been prepared from the chiral pool. The corresponding N‐heterocyclic carbenes were evaluated as organocatalysts in three enantioselective reactions involving homoenolate intermediates generated from enals. The catalysts proved competent in enantioselective cyclopentannulation and γ‐lactonization reactions, a premiere for imidazoline‐based NHCs. This work conveys some new ideas and knowledge on the concepts of bifunctional enantioselective organocatalysis applied to NHCs.