Enantioselective [4 + 2] Cycloaddition of Cyclic <i>N</i>-Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones

Abstract

A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.