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Catalytic Enantio- and Diastereoselective Aldol Reactions of Glycine-Derived Silicon Enolate with Aldehydes: An Efficient Approach to the Asymmetric Synthesis of anti-β-Hydroxy-α-Amino Acid Derivatives

Jun Kobayashi, Masayuki Nakamura, Yuichiro Mori, Yasuhiro Yamashita and Shu Kobayashi*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: skobayasmol.f.u-tokyo.ac.jp

J. Kobayashi, M. Nakamura, Y. Mori, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc., 2004, 126, 9192-9193.

DOI: 10.1021/ja047597t (free Supporting Information)


Abstract

An efficient method for the asymmetric synthesis of anti-β-hydroxy-α-amino acid derivatives is based on highly enantio- and diastereoselective aldol reactions of the silicon enolate derived from N-trifluoroacetylglycinate with aldehydes using a chiral zirconium catalyst.

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Key Words

α-Amino Acid Derivatives, Mukaiyama Aldol Addition


ID: J48-Y2004-1620