Organic Chemistry Portal >
Reactions > Organic Synthesis Search

Categories: N=S Bond Formation >

Synthesis of sulfoximines


Recent Literature

A rhodium-catalyzed transfer of carbamates to sulfoxides enables a convenient synthesis of N-protected sulfoximines under mild conditions. Sulfoximines, including 4-membered thietane-oximines, bearing Boc and Cbz groups are readily deprotected.
M. Zenzola, R. Doran, R. Luisi, J. A. Bull, J. Org. Chem., 2015, 80, 6391-6399.

In a preparation of N-alkyl-substituted sulfoximines from sulfides, in situ generated N-bromoalkylamines serve as readily accessible imidating agents leading to N-alkylsulfiliminium bromides that are subsequently oxidized providing the desired products. This unprecedented one-pot imidation/oxidation sequence provides gram quantities of product in a short period of time avoiding the use of toxic alkylating reagents.
C. A. Dannenberg, V. Bizet, C. Bolm, Synthesis, 2015, 47, 1951-1959.

An iron(II)-catalyzed nitrene transfer reaction of sulfoxides with N-acyloxyamides provides N-acyl sulfoximines with high functional-group compatibility. The transformation was carried out under an air atmosphere at ambient temperature and could be scaled up to gram scale with a low catalyst loading.
T. Qi, N. Fang, W. Huang, J. Chen, Y. Luo, Y. Xia, Org. Lett., 2022, 24, 5674-5678.

Sulfoximines, sulfilimines, sulfinimides, sulfonimidates and sulfonimidamides - the chiral sulfur connection