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Issue 18, 1994
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(E)-stereoselective synthesis of vinylglycines from (R)-serine via organocopper–BF3 and related reagents

Abstract

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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Article information


J. Chem. Soc., Chem. Commun., 1994, 2151-2152
Article type
Paper

(E)-stereoselective synthesis of vinylglycines from (R)-serine via organocopper–BF3 and related reagents

T. Ibuka, K. Suzuki, H. Habashita, A. Otaka, H. Tamamura, N. Mimura, Y. Miwa, T. Taga and N. Fujii, J. Chem. Soc., Chem. Commun., 1994, 2151 DOI: 10.1039/C39940002151

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