Design, Synthesis, and Organocatalytic Activity of N-Heterocyclic Carbenes Functionalized with Hydrogen-Bond Donors in Enantioselective Reactions of Homoenolates - Aix-Marseille Université Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2013

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

Faisal Nawaz
  • Function : Author
Mehdi Zaghouani
  • Function : Author
Damien Bonne
Olivier Chuzel
Jean Rodriguez
  • Function : Author
  • PersonId : 921781
Yoann Coquerel

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.

Dates and versions

hal-00979187 , version 1 (15-04-2014)

Identifiers

Cite

Faisal Nawaz, Mehdi Zaghouani, Damien Bonne, Olivier Chuzel, Jean Rodriguez, et al.. Design, Synthesis, and Organocatalytic Activity of N-Heterocyclic Carbenes Functionalized with Hydrogen-Bond Donors in Enantioselective Reactions of Homoenolates. European Journal of Organic Chemistry, 2013, 36, pp.8253-8264. ⟨10.1002/ejoc.201301366⟩. ⟨hal-00979187⟩
49 View
0 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More