Dienylation of N-benzoylhydrazones with CF3-substituted homoallenylboronates in water

A convenient method for the dienylation of N-benzoylhydrazones in water has been developed. This protocol expanded the synthetic application of functionalized homoallenylboronates to provide the useful 2-aminomethyl-1,3-diene derivatives with high efficiency (up to 99% yield) and stereoselectivity w...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-02, Vol.20 (7), p.1386-1390
Main Authors: Wei-Wei, Ma, Yang, Chao, Xie, Qiang, Yun-He, Xu
Format: Article
Language:English
Subjects:
Catalysts
Inert atmospheres
Pyrrolidine
Stereoselectivity
Online Access:Get full text
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Summary:A convenient method for the dienylation of N-benzoylhydrazones in water has been developed. This protocol expanded the synthetic application of functionalized homoallenylboronates to provide the useful 2-aminomethyl-1,3-diene derivatives with high efficiency (up to 99% yield) and stereoselectivity without using any catalyst, additive or inert atmosphere. Furthermore, the transformation of a 2-aminomethyl-1,3-diene derivative to synthesize a functionalized pyrrolidine derivative was also explored.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob02335g