Previous general methods for the preparation of cyclic sulfinamides are hampered by limited substrate scope, due to the necessity of a phenyl ring in the construction of the benzofused cyclic sulfoximine intermediate. A novel synthesis of cyclic sulfinamides 5 is presented, which proceeds via the sigmatropic rearrangement of 2-vinylaziridines 3 to non-fused cyclic sulfoximines 4. The telescoped protocol is diastereoselective and affords the cyclic sulfinamides 5, from readily available sulfinimines 1, in only 2 steps. Current work is focused on exploring the scope of a novel ring contraction of mesityl sulfoximines 4 to 3-pyrrolines 6.

Cyclic sulfoximines: Useful building blocks for the expedient synthesis of cyclic sulfinamides and 3-pyrrolines

255th National Meeting (2018)

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