Asymmetric syntheses of all four 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.

altmetric score

  • 3

author list (cited authors)

  • Burgess, K., & Ho, K. K.

citation count

  • 47

publication date

  • October 1992