Tetrahedron Letters

Preparation of vinylglycines by thermolysis of homocysteine sulfoxides

SK Patel, TE Long

Index: Patel, Sravan Kumar; Long, Timothy E. Tetrahedron Letters, 2009 ,  vol. 50,  # 36  p. 5067 - 5070

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Citation Number: 6

Abstract

The synthesis and efficacy of preparing Cbz-VG-OMe (1) by thermolysis of alkyl and aryl homocysteine sulfoxides were surveyed. This investigation determined that aryl sulfoxide analogs were more effective for the reaction and that the 2-nitrophenyl analog 10f possessed a unique ability to syn eliminate at temperatures as low as 100° C. The thermolysis of sulfoxide 10f was additionally discovered to occur under toluene reflux and ...