期刊
NATURE PROTOCOLS
卷 8, 期 11, 页码 2271-2280出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/nprot.2013.134
关键词
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资金
- US National Science Foundation [CHE-1049571]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1049571] Funding Source: National Science Foundation
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.
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