Categories: C-S Bond Formation >
Synthesis of sulfoximines
A one-pot approach to both sulfoximines and sulfonimidamides exploits the high electrophilicity of sulfinyl nitrenes. These rare reactive intermediates are generated from a sulfinylhydroxylamine (R-O-N=S=O) reagent through an N-O bond fragmentation process. Addition of carbon and nitrogen nucleophiles enables the synthesis of sulfoximines and sulfonimidamides in just 15 min.
T. Q. Davis, M. J. Tilby, J. Ren, N. A. Parker, D. Skolc, A. Hall, F. Duarte, M. C. Willis, J. Am. Chem. Soc., 2020, 142, 15445-15453.
Chiral sulfoximines are promising bioisosteres in medicinal chemistry. A stereospecific S-alkylation of readily accessible chiral sulfinamides enables an asymmetric synthesis of chiral sulfoximines under practical conditions.
Y. Maeda, S. Hamada, Y. Aota, K. Otsubo, T. Kano, K. Maruoka, J. Org. Chem., 2022, 87, 3652-3660.
A sulfur-selective arylation of easily accessible chiral sulfinamides enables an asymmetric synthesis of chiral sulfoximines. The utility of the present method is demonstrated by the asymmetric synthesis of a key intermediate of a COX-2 inhibitor.
Y. Aota, T. Kano, K. Maruoka, J. Am. Chem. Soc., 2019, 141, 19263-19268.
Visible light mediates a reaction of N-tosyl-protected sulfoximidoyl chlorides with aryl alkynes in the presence of air and a ruthenium photocatalyst to provide β-keto sulfoximines in good yields. The reaction offers high functional group tolerance.
P. Shi, Y. Tu, C. Wang, D. Ma, C. Bolm, J. Org. Chem., 2022, 87, 3817-3824.