Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an efficient approach to the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives |
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Authors: | Kobayashi Jun Nakamura Masayuki Mori Yuichiro Yamashita Yasuhiro Kobayashi Shu |
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Affiliation: | Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. |
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Abstract: | We have developed an efficient method for the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives based on highly enantio- and diastereoselective aldol reactions of the silicon enolate derived from N-trifluoroacetylglycinate with aldehydes using a chiral zirconium catalyst. The resulting N-trifluoroacetyl group is easily cleaved under either acidic or basic conditions and can be used directly as a protecting group for further transformations. |
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