Journal
CHEMICAL SCIENCE
Volume 11, Issue 18, Pages 4741-4746Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc00683a
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Funding
- National Natural Science Foundation of China [21572092]
- Natural Science Foundation of Gansu Province [18JR4RA003]
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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 alpha-alkyl alpha-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.
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