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In Situ Catalyst Improvement in the Proline-Mediated α-Amination of Aldehydes

Journal of the American Chemical SocietyPublished 1 September 2004
Hiroshi Iwamura, Suju Mathew, Donna G. Blackmond
Citations113
SJR quartileQ1
SJR score5.55
SNIP2.61

TL;DR

Kinetic investigations show that the proline-mediated α-amination of aldehydes exhibits autoinductive rate behavior and amplification of product enantiomeric excess, which implicate amino acid catalysis in rationalizations of the origin of biological homochirality.

Abstract

Kinetic investigations show that the proline-mediated alpha-amination of aldehydes exhibits autoinductive rate behavior and amplification of product enantiomeric excess. Further experiments highlight the role of product, offering suggestions for the design of catalysts of improved efficiency for such transformations. The unusual characteristics exhibited by these reactions implicate amino acid catalysis in rationalizations of the origin of biological homochirality.

Keywords

ChemistryBiochemistry, Genetics and Molecular Biology