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Synfacts 2011(10): 1127-1127
DOI: 10.1055/s-0030-1261125
DOI: 10.1055/s-0030-1261125
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of α-Amino Acid Derivatives by Biomimetic Transamination
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
Further Information
Publication History
Publication Date:
20 September 2011 (online)
Significance
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.