Synthesis, Reactivity and Application of Vinyl Sulfoximines and Vinyl Aminosulfoxonium Salts

Abstract

AbstractThe combination of a sulfonimidoyl and aminosulfoxonium group with a double bond renders vinyl sulfoximines and vinyl aminosulfoxonium salts particularly versatile classes of compounds in organic synthesis. The discussion of vinyl sulfoximines includes in addition to the synthesis, the Michael reaction and its application in asymmetric synthesis, the synthesis, structure and application of α‐lithiovinyl sulfoximines, the nickel‐catalyzed and copper‐mediated anionic cross‐coupling reaction of α‐metallovinyl sulfoximines, the synthesis of acyclic and cyclic dienyl vinyl sulfoximines and the ring‐closing metathesis, the hydroalumination and reductive Pauson‐Khand reaction, the nickel‐catalyzed cross‐coupling reaction, the vinyl‐allyl isomerization, the cycloaddition, and the cyclization. The discussion of vinyl aminosulfoxonium salts includes in addition to the synthesis, the Michael reaction, the ethylenation of protic nucleophiles, the synthesis of allyl aminosulfoxonium salts and the nucleophilic substitution, the synthesis of allyl aminosulfoxonium ylides and the imino ester aziridination, the synthesis of vinyl aminosulfoxonium ylides, the synthesis of alkynes and dihydrofurans, the nickel‐catalyzed cross‐coupling reaction, and the intramolecular substitution of the amino group.