In situ catalyst improvement in the proline-mediated alpha-amination of aldehydes

Journal of the American Chemical Society
Hiroshi IwamuraDonna G Blackmond

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.

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Citations

May 17, 2011·Journal of the American Chemical Society·Jordi BurésDonna G Blackmond
May 29, 2012·Journal of the American Chemical Society·Nongnaphat DuangdeeAlbrecht Berkessel
Oct 2, 2009·Journal of the American Chemical Society·Markus WiesnerHelma Wennemers
Dec 3, 2005·Organic Letters·Cory S BesharaNicholas C O Tomkinson
Oct 19, 2006·Chemical Communications : Chem Comm·Suju P MathewDonna G Blackmond
Aug 19, 2007·Chemical Communications : Chem Comm·Stefan BräseHenning Vogt
Aug 9, 2008·Chemical Communications : Chem Comm·Mohamed Amedjkouh, Maria Brandberg
Feb 15, 2014·Organic & Biomolecular Chemistry·Akira YanagisawaKazuhiro Yoshida
Jan 17, 2016·Journal of the American Chemical Society·Melissa A AshleyMathew J Vetticatt
Jun 2, 2006·Nature·Martin KlussmannDonna G Blackmond
Aug 3, 2017·Organic & Biomolecular Chemistry·Jyoti DuttaShraeddha Tiwari
Mar 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tirayut Vilaivan, Worawan Bhanthumnavin
Apr 23, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Christopher BeattiePedro Villuendas
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Oct 25, 2006·Angewandte Chemie·Martin KlussmannDonna G Blackmond
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