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Synthesis of sulfoximines
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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 |