Abstract
AbstractA novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides access to complex chiral sulfoximines in only two steps from commercially available aldehydes. A mechanistic hypothesis and synthetic application in the formal synthesis of trachelanthamidine, by transformation of a cyclic sulfoximine into a pyrroline, is also disclosed.
Highlights
A novel rearrangement of 2-vinyl aziridine 2-carboxylates to unusual chiral cyclic sulfoximines is described
The rearrangement seemed tolerant of sterically hindered alkylaziridines, which transformed into the corresponding sulfoximines in good yields (Entries 2, 3)
In the case of aziridine 2a, we noted that both the two diastereomeric aziridines formed from the corresponding sulfinimine rearranged to the same cyclic sulfoximine 3a
Summary
A novel rearrangement of 2-vinyl aziridine 2-carboxylates to unusual chiral cyclic sulfoximines is described . Several aziridines were synthesised following our previously reported method,15 which were subsequently submitted to the rearrangement reaction conditions (Table 2).
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