Advances in N‐Heterocyclic Carbene Catalysis for Natural Product Synthesis
Yonglei Que, Haibing He
Abstract
N‐heterocyclic carbenes (NHCs) efficiently catalyze new bond formations with high regio‐ and stereoselectivity through umpolung and non‐umpolung processes. These processes typically involve four species: Breslow intermediates, homoenolates, enolates, and α,β‐unsaturated acyl azoliums. Organic syntheses are increasingly relying on NHC catalysis, and this minireview highlights developments in NHC‐catalyzed reactions that, over the past two decades, have been used as key steps in the total syntheses of natural products. Crucial intermediates and reaction mechanisms are presented in detail.
Topics & Concepts
UmpolungChemistryCarbeneNatural productStereoselectivityCatalysisOrganocatalysisOrganic chemistryCombinatorial chemistryEnantioselective synthesisNucleophileN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods