Va. Soloshonok et al., HIGHLY DIASTEREOSELECTIVE ASYMMETRIC ALDOL REACTIONS OF CHIRAL NI(II)-COMPLEX OF GLYCINE WITH ALKYL TRIFLUOROMETHYL KETONES, Tetrahedron : asymmetry, 7(6), 1996, pp. 1547-1550
Asymmetric aldol reactions between prochiral trifluoromethyl ketones a
nd Ni(II)-complex of monochiral Schiff base of glycine with (S)-o-[N-(
N-benzylprolyl)amino]benzophenone (BBP) are described. General stereod
irecting features of the trifluoromethyl group controlling (2S,3S)-abs
olute configuration (90-98 %de) of the resultant amino acids is demons
trated. New set of reaction conditions allowing preparative synthesis
of diastereo, and enantiomerically pure (2S,3S)-3-trifluoromethyl-3-su
bstituted serines of biomedicinal interest is presented. (C) 1996 Else
vier Science Ltd