Stereoselective epoxidation of vinyl sulfones and N-(p-tolylsulfonyl)vinylsulfoximines derived from isopropylideneglyceraldehyde: synthesis of chiralbuilding blocks
Ad. Briggs et al., Stereoselective epoxidation of vinyl sulfones and N-(p-tolylsulfonyl)vinylsulfoximines derived from isopropylideneglyceraldehyde: synthesis of chiralbuilding blocks, J CHEM S P1, (24), 1998, pp. 4097-4102
Epoxidation of N-(p-tolylsulfonyl)vinylsulfosimines using metal alkyl perox
ides proceeds with varying degrees of stereoselectivity, depending both on
the metal cation and the steric bulk of the alkyl peroxide group. The stere
ochemical outcome of the epoxidation of substrates bearing an allylic asymm
etric centre is also dependent upon the epoxidising agent, and very high le
vels of stereoselectivity may be obtained in the formation of sulfonyloxira
ne 8a. This oxirane was subsequently converted into the sulfonyloxirane 15,
a precursor to a useful chiral functionalised acyl anion equivalent. In ad
dition, the optically pure alpha-bromothioester 20 was also prepared.