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

Kinetic investigations show that the proline-mediated α-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 tr...

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Veröffentlicht in:	Journal of the American Chemical Society 2004-09, Vol.126 (38), p.11770-11771
Hauptverfasser:	Iwamura, Hiroshi, Mathew, Suju P, Blackmond, Donna G
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Amination Catalysis Chemistry Exact sciences and technology Kinetics Organic chemistry Proline - chemistry
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	Kinetic investigations show that the proline-mediated α-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.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja046258x