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DOI: 10.1055/s-0030-1261125
Synthesis of α-Amino Acid Derivatives by Biomimetic Transamination
Contributor(s):Benjamin List, Qinggang WangInstitute 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
Publication History
Publication Date:
20 September 2011 (online)
Key words
biomimetic transamination - amino acids -
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.
Comment
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.