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Convenient Route to Secondary Sulfinates: Application to the Stereospecific Synthesis of α-C-Chiral Sulfonamides

Michael G. Johnson, Michael W. Gribble, Jr., Jonathan B. Houze and Nick A. Paras*

*Department of Therapeutic Discovery, Amgen, Inc., 1120 Veterans Boulevard, South San Francisco, California 94080, United States, Email: nick.parasucsf.edu

M. G. Johson, M. W. Gribble Jr., J. B. Houze, N. A. Paras, Org. Lett., 2014, 16, 6248-6251.

DOI: 10.1021/ol503208z


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Abstract

Heterocyclic thioethers and sulfones serve as readily available precursors for a convenient synthesis of α-chiral sulfinates. Treatment of the sulfinates with hydroxylamine sulfonate in aqueous solution provides α-C-chiral primary sulfonamides in good yield with retention of stereochemical purity.


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Synthesis of α-C-Stereochemically Pure Secondary Sulfonamides

V. A. Andriashvili, S. Zhersh, A. A. Tolmachev, O. O. Grygorenko, J. Org. Chem., 2022, 87, 6237-6246.


Key Words

sulfonamides, sulfinates


ID: J54-Y2014