Asymmetric reactions of N-heterocyclic carbene (NHC)-based chiral acyl azoliums and azolium enolates

Abstract

N-Heterocyclic carbene (NHC) organocatalysis has been recognized as a powerful synthetic strategy for the construction of a wide variety of medicinally and biologically important molecules. Although NHCs are known as the umpolung of aldehydes, NHC-based species involving non-umpolung processes have attracted considerable attention over the past decade because of their diverse reactivity and applicability to asymmetric reactions. Previous reviews focused mainly on the reactions of α,β-unsaturated acyl azoliums, while the current review focuses on the generation and application of other NHC-based intermediates including α,β-unsaturated alkynyl acyl azoliums, dienyl acyl azoliums, azolium enolates, azolium dienolates, azolium allenolates, and cumulenol in asymmetric transformations since 2010.

Keywords

• N-Heterocyclic carbenes
• Organocatalysis
• Asymmetric synthesis
• Acyl azoliums
• Enolates