Enantioselective aerobic oxidative cross-dehydrogenative coupling of glycine derivatives with ketones and aldehydes via cooperative photoredox catalysis and organocatalysis. Issue 18 (27th April 2020)

• Record Type: Journal Article
• Authors: Yang, Xiaorong; Xie, Zhixiang; Li, Ying; Zhang, Yuan
• Is Part Of: Chemical science. Volume 11:Issue 18(2020)
• Page Start: 4741
• Page End: 4746
• Publication Date: 2020-04-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc00683a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A visible-light-induced enantioselective aerobic oxidative cross-dehydrogenative coupling between glycine derivatives and simple ketones or aldehydes is achieved. Abstract : The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective aerobic oxidative cross-dehydrogenative coupling between glycine derivatives and simple ketones or aldehydes, which provides an efficient approach for the rapid synthesis of enantiopure unnatural α-alkyl α-amino acid derivatives in good yield with excellent diastereo- (up to >99 : 1) and enantioselectivities (up to 97% ee). This process includes the direct photoinduced oxidation of glycine derivatives to an imine intermediate, followed by the asymmetric Mannich-type reaction with an enamine intermediate generated in situ from a ketone or aldehyde and a chiral secondary amine organocatalyst. This mild method allows the direct formation of a C–C bond with simultaneous installation of two new stereocenters without wasteful removal of functional groups.