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The stereoselective synthesis of biologically important vinylglycine derivatives by reaction of homochiral 4-methoxycarbonyl-5-vinyloxazolidin-2-ones with organocopper reagents is described; 4,5-trans-oxazolidin-2-one 6 yields (E)-vinylglycines as the major products by treatment with the ‘higher order’ cyanocuprate–BF3 reagents or trialkylzincates in the presence of cuprous cyanide, 4,5-cis-oxazolidin-2-one 10 affords only the desired (E)-vinylglycines.
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Ibuka et al. (1994) studied this question.
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