Petasis-Type gem-Difluoroallylation Reactions Assisted by the Neighboring Hydroxyl Group in Amines

Petasis-Type gem-Difluoroallylation Reactions Assisted by the Neighboring Hydroxyl Group in Amines

A three-component Petasis-type gem-difluoroallylation reaction of using pinacol gem-difluoroallylboronates, aldehydes or isatin, and β-amino alcohols enabled by the neighboring hydroxyl group in amine is reported, affording various racemic and chiral gem-difluorohomoallylamine derivatives with good...

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Veröffentlicht in:Organic letters 2018-05, Vol.20 (9), p.2585-2589
Hauptverfasser: Yang, Xing, Cao, Ze-Hun, Zhou, Yang, Cheng, Feng, Lin, Zi-Wei, Ou, Zhi, Yuan, Ye, Huang, Yi-Yong
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container_end_page 2589
container_issue 9
container_start_page 2585
container_title Organic letters
container_volume 20
creator Yang, Xing
Cao, Ze-Hun
Zhou, Yang
Cheng, Feng
Lin, Zi-Wei
Ou, Zhi
Yuan, Ye
Huang, Yi-Yong
description A three-component Petasis-type gem-difluoroallylation reaction of using pinacol gem-difluoroallylboronates, aldehydes or isatin, and β-amino alcohols enabled by the neighboring hydroxyl group in amine is reported, affording various racemic and chiral gem-difluorohomoallylamine derivatives with good to excellent results. Based on the control experiment and stereochemistry of the product, a proposed reaction pathway is illustrated to clarify the origin of regio- and stereoselectivity under protic solvent conditions.
doi_str_mv 10.1021/acs.orglett.8b00721
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title Petasis-Type gem-Difluoroallylation Reactions Assisted by the Neighboring Hydroxyl Group in Amines
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