Intramolecular Umpolung Synthesis of Exocyclic β-Amino Alcohols through Decarboxylative Amination | Zendy

Jianfeng Chen | Zendy; Jiaxin Tian | Zendy; Feng Liu | Zendy; Yong Liu | Zendy; Guoqing Zhao | Zendy; WeiCheng Yuan | Zendy; Baoguo Zhao | Zendy

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

Author(s) -

Jianfeng Chen,

Jiaxin Tian,

Feng Liu,

Yong Liu,

Guoqing Zhao,

WeiCheng Yuan,

Baoguo Zhao

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b02324

Subject(s) - umpolung , intramolecular force , amination , chemistry , organic chemistry , amino acid , combinatorial chemistry , catalysis , biochemistry , nucleophile

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.

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