American Chemical Society
ao8b02324_si_002.cif (243.69 kB)

Intramolecular Umpolung Synthesis of Exocyclic β‑Amino Alcohols through Decarboxylative Amination

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posted on 2018-11-01, 18:06 authored by Jianfeng Chen, Jiaxin Tian, Feng Liu, Yong Liu, Guoqing Zhao, Weicheng Yuan, Baoguo Zhao
An intramolecular aminative Umpolung cyclization strategy has been developed by using α,α-diphenylglycine (2) as the amination and Umpolung reagent. Aldehydes (1) bearing an additional carbonyl group underwent condensation with α,α-diphenylglycine to form an imine, decarboxylation to generate a delocalized 2-azaallylanion, and subsequent intramolecular Umpolung cyclization to produce a variety of exocyclic β-amino alcohols (6) in 60–93% yields with up to >20:1 trans/cis selectivity under mild conditions.