title: Asymmetric synthesis of amines using tert-butanesulfinamide.
abstract: Chiral amines are prevalent in many bioactive molecules, including amino acids and pharmaceutical agents. tert-Butanesulfinamide (tBS) is a chiral amine reagent that has enabled the reliable asymmetric synthesis of a very broad range of different amine structures from simple, readily available starting materials. Three steps are commonly applied to the asymmetric synthesis of amines: (i) condensation of tBS with a carbonyl compound, (ii) nucleophile addition and (iii) tert-butanesulfinyl group cleavage. Here we demonstrate these steps with the preparation of a propargylic tertiary carbinamine, one of a class of amines that have been used for many different biological purposes, including click chemistry applications, diversity-oriented synthesis, the preparation of peptide isosteres and the development of protease inhibitors as drug candidates and imaging agents. The process described here can be performed in 3-4 d.
authors.affiliation: 1] Department of Chemistry, Yale University, New Haven, Connecticut, USA. [2] Department of Chemistry, Xiamen University, Xiamen, China.
authors.forename: Hai-Chao
authors.initials: HC
authors.lastname: Xu
authors.forename: Somenath
authors.initials: S
authors.lastname: Chowdhury
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D000588:Amines / Q000138:chemical synthesis*; D002073:Butanes / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000588:Amines; D002073:Butanes; D013449:Sulfonamides; C511422:tert-butanesulfinamide