Highly enantioselective α-sulfenylation of 5H-oxazol-4-ones to N-(sulfanyl)succinimides

An unprecedented asymmetric α-sulfenylation of 5H-oxazol-4-ones to N-(sulfanyl)succinimides has been established, to access various α-sulfenylated adducts with good to excellent enantioselectivities (86–95% ee) by utilizing a cinchona alkaloid-derived squaramide as catalyst. The conditions of this α-sulfenylation protocol simultaneously satisfy N-(arylthio)succinimides, N-(benzylthio)succinimides, and N-(alkylthio)succinimides by tuning the substituted groups of 5H-oxazol-4-ones on the 2-position as well as additives.

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