Asymmetric synthesis of amines using tert-butanesulfinamide.
Nat Protoc, 2013/11;8(11):2271-80.
Xu HC[1], Chowdhury S, Ellman JA
Affiliations
PMID: 24157547DOI: 10.1038/nprot.2013.134
Impact factor: 17.021
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.
MeSH terms
More resources
EndNote: Download