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Synfacts 2011(10): 1104-1104  
DOI: 10.1055/s-0030-1261138
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Conjugate Addition Approach Towards Unnatural Amino Acid Derivatives

Contributor(s): Mark Lautens, Stephen G. Newman
Z.-Y. Xue, Q.-H. Li, H.-Y. Tao, C.-J. Wang*
Wuhan University and Nankai University, Tianjin, P. R. of China
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Publication Date:
20 September 2011 (online)

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Significance

Unnatural α-amino acids play important roles in peptide-based drugs and iso­steres. The preparation of unnatural amino acids in high stereochemical purity is a challenging and important task. In the present work, β-substituted bisphosphonates are explored as Michael acceptors. Utilizing azomethine ylid nucleophiles, unnatural α-amino acids containing two adjacent tertiary stereogenic centers are produced in excellent yield, diastereoselectivity, and enantioselectivity.