Synthesis of α-Amino Acid Derivatives by Biomimetic
Transamination

doi:10.1055/s-0030-1261125

Synfacts 2011(10): 1127-1127
DOI: 10.1055/s-0030-1261125

Organo- and Biocatalysis

Synthesis of α-Amino Acid Derivatives by Biomimetic Transamination

Contributor(s):Benjamin List, Qinggang Wang

X. Xiao, Y. Xie, C. Su, M. Liu, Y. Shi*
Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. of China and Colorado State University, Fort Collins, USA
Organocatalytic Asymmetric Biomimetic Transamination: From α-Keto Esters to Optically Active α-Amino Acid Derivatives
J. Am. Chem. Soc. 2011, 133: 12914-12917

Abstract

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Key words

biomimetic transamination - amino acids -

Significance

<P>Shi and co-workers have developed a methodology to synthesize α-amino acid derivatives 3 from α-keto esters 2, catalyzed by cinchona alkaloid derivative 1. This is the first catalytic highly enantioselective synthesis of α-amino acid derivatives 3 via biomimetic transamination. The proton of the ammonium ion in the transition state is delivered to the si-face of the substrate, affording the (R)-α-amino ester as the major enantiomer.</P>

Comment

<P>Optically active α-amino acids and their derivatives are an important class of molecules in biology and in organic synthesis. However, it remains a challenge to develop highly enantioselective syntheses of them to date. Here, a very efficient method for the synthesis of α-amino acid derivatives via biomimetic transamination has been reported, which also illustrates the synthetic potential of organocatalytic biomimetic transamination.</P>

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