Recent Developments on Brønsted Acid Catalyzed Asymmetric Aldol Reactions and the Fate of the Catalysts

Abstract

Since the innovative work of Terada and Akiyama, asymmetric reaction using chiral Brønsted acid has attracted great attention. Asymmetric aldol reactions are extensively studied in different organocatalysis. Brønsted acid-catalyzed aldol reaction may be carried out directly without modification of the substrates or Mukaiyama type aldol reaction using silyl enol ether as nucleophiles. The reaction may proceed through the formation of enol intermediate followed by the attack to the electrophile while Mukaiyama type aldol reactions may follow two mechanistic pathways- Brønsted acidic pathways where Brønsted acid directly activates the substrate or Lewis acid pathways where Brønsted acid acts as pre-catalyst. Here, the recent advancement of asymmetric aldol reactions using chiral Brønsted acid as a catalyst and the fate of the catalysts in the reaction has been discussed in this review. It is observed that some kinds of aldol reactions have rarely been studied and need more attention.