ASYMMETRIC SYNTHESES OF ALL 4 STEREOISOMERS OF 2,3-METHANOMETHIONINE Academic Article uri icon

abstract

  • Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine ((Z)- and (E)-cyclo-Met) are described. The source of chirality in these reactions is the trifluoromethylsulfonate ester lb which reacts with di-tert-butyl malonate via direct displacement of trifluoromethylsulfonate followed by lactonization to give 1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo[3.1.0]hexane (2). Conversion of compound 2 into (Z)-cyclo-Met can be achieved via ring opening of the lactone, Hoffmann rearrangement, mesylation, and displacement with thiomethoxide. A route to (E)-cyclo-Met was developed using a lipase to effect a critical ester hydrolysis. 1992, American Chemical Society. All rights reserved.

published proceedings

  • JOURNAL OF ORGANIC CHEMISTRY

altmetric score

  • 3

author list (cited authors)

  • BURGESS, K., & HO, K. K.

citation count

  • 62

complete list of authors

  • BURGESS, K||HO, KK

publication date

  • October 1992