Rf. Delapradilla et al., HIGHLY STEREOSELECTIVE NUCLEOPHILIC EPOXIDATION OF SIMPLE VINYL SULFOXIDES, Journal of organic chemistry, 63(15), 1998, pp. 4954-4966
The nucleophilic epoxidation of readily available vinyl and dienyl sul
foxides with MOO-t-Bu (M = Li, Na, K) takes place in good yields, with
complete preservation of double bond geometry in most cases and with
moderate to excellent diastereofacial selectivity to produce enantio-
and diastereomerically pure cr,P-epoxy sulfoxides, valuable synthetic
intermediates. Subsequent straightforward oxidation at sulfur affords
the corresponding enantiopure sulfonyl oxiranes. For (1E)-2-sulfinyl d
ienes, the facial selectivity of this novel process may be controlled
by the choice of metal (Li vs Na).