Asymmetric synthesis of amines using tert-butanesulfinamide

作者：Xu, Hai-Chao; Chowdhury, Somenath; Ellman, Jonathan A.^*

来源：Nature Protocols, 2013, 8(11): 2271-2280.

DOI：10.1038/nprot.2013.134

• CATHEPSIN-S
• ARYLBORONIC ACIDS
• DIASTEREOSELECTIVE SYNTHESIS
• ORGANOMETALLIC REAGENTS
• NONPEPTIDIC INHIBITORS
• DIRECT CONDENSATION
• CHIRAL AMINES
• IDENTIFICATION
• ALDEHYDES
• ADDITIONS

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.

• 出版日期2013-11
• 单位厦门大学