Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines

Abstract

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Diastereoselective Aza‐Mislow–Evans Rearrangement of N‐Acyl tert‐Butanesulfinamides into α‐Sulfenyloxy Carboxamides

“…Furthermore, replacing the sulfoxide oxygen atom with a functionalized nitrogen atom has expanded the substrate scope to include allylic sulfimides . However, relatively few sigmatropic rearrangement reactions involving sulfinamides have been reported, in contrast to the widespread use of rearrangements involving functionalized allylic sulfoxides.…”

“…[3] Recent studies of the Mislow-Evans rearrangement have focused on incorporating the rearrangement into sequential transformations, [4] thereby expanding synthetic applications. [6] However,relatively few sigmatropic rearrangement reactions involving sulfinamides have been reported, [7] in contrast to the widespread use of rearrangements involving functionalized allylic sulfoxides. [6] However,relatively few sigmatropic rearrangement reactions involving sulfinamides have been reported, [7] in contrast to the widespread use of rearrangements involving functionalized allylic sulfoxides.…”

Efficient Synthesis of Cyclic Sulfoximines from N‐Propargylsulfinamides through Sulfur–Carbon Bond Formation

“…Among sulfoximines, cyclic ones belong to an underutilized class of heterocycles, whose potential biological properties remain largely unexplored. Only a few methods including the 3+2 cycloaddition between N‐sulfinylimines and in situ generated benzynes and the sigmatropic rearrangement of N‐sulfinyl‐2‐vinylaziridines have so far been reported to produce cyclic sulfoximines from sulfinamide starting materials (Scheme b) . Very recently, Poisson et al.…”

Olefination of N‐Sulfinylimines under Mild Conditions

“…Electrophilic imines have attracted much interest recently as a result of their simple preparation, their usefulness as directing groups, and their inherent reactivity in addition reactions in organic chemistry . In particular, N ‐protected imines, including N ‐sulfinyl, N ‐phosphonyl, N ‐phosphoryl, and N ‐phosphinyl imines, have been used as chiral auxiliaries in nucleophilic addition reactions.…”