title: Convenient route to secondary sulfinates: application to the stereospecific synthesis of α-C-chiral sulfonamides.
abstract: A convenient synthesis of α-chiral sulfinates from readily available precursors has been accomplished via the corresponding heterocyclic thioethers and sulfones. Treatment of the sulfinates with hydroxylamine sulfonate in aqueous solution provides α-C-chiral primary sulfonamides in good yield (14 examples) with retention of stereochemical purity.
authors.affiliation: Department of Therapeutic Discovery, Amgen, Inc., 1120 Veterans Boulevard, South San Francisco, California 94080, United States.
authors.forename: Michael G
authors.initials: MG
authors.lastname: Johnson
authors.affiliation: Department of Therapeutic Discovery, Amgen, Inc., 1120 Veterans Boulevard, South San Francisco, California 94080, United States.
authors.forename: Michael W
authors.initials: MW
authors.lastname: Gribble
authors.affiliation: Department of Therapeutic Discovery, Amgen, Inc., 1120 Veterans Boulevard, South San Francisco, California 94080, United States.
authors.forename: Jonathan B
authors.initials: JB
authors.lastname: Houze
authors.affiliation: Department of Therapeutic Discovery, Amgen, Inc., 1120 Veterans Boulevard, South San Francisco, California 94080, United States.
authors.forename: Nick A
authors.initials: NA
authors.lastname: Paras
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013441:Sulfinic Acids; D013449:Sulfonamides