(S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: ideal Michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives.
[formula: see text] Enantiomerically pure (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones were found to serve as ideal Michael acceptors in addition reactions with achiral Ni(II) complexes of glycine Schiff bases. Virtually complete control of simple and face diastereoselectivity, observed in these reactions, combined with quantitative chemical yields renders this methodology synthetically superior to the previous methods.
Soloshonok
V A
VA
Department of Chemistry, University of Arizona, Tucson 85721, USA. vadym@u.arizona.edu
Cai
C
C
Hruby
V J
VJ
D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010080:Oxazoles; D005998:Glycine