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.
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.
Kobayashi
Jun
J
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Nakamura
Masayuki
M
Mori
Yuichiro
Y
Yamashita
Yasuhiro
Y
Kobayashi
Shu
S
D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D005463:Fluoroacetates; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D006880:Hydroxy Acids / Q000138:chemical synthesis*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry
D000447:Aldehydes; D000596:Amino Acids; D005463:Fluoroacetates; D006880:Hydroxy Acids; D015040:Zirconium; D005998:Glycine; D012825:Silicon