A Quinine-Squaramide Catalyzed Enantioselective Aza-Friedel-Crafts Reaction of Cyclic Trifluoromethyl Ketimines with Naphthols and Electron-Rich Phenols

Ding Zhou; Zheng Huang; Xueting Yu; Youxin Wang; Jian Li; Wei Wang; Hexin Xie

doi:10.1021/acs.orglett.5b02668

A Quinine-Squaramide Catalyzed Enantioselective Aza-Friedel-Crafts Reaction of Cyclic Trifluoromethyl Ketimines with Naphthols and Electron-Rich Phenols

Ding Zhou, Zheng Huang, Xueting Yu, Youxin Wang, Jian Li, Wei Wang, Hexin Xie

Research output: Contribution to journal › Article › peer-review

78 Scopus citations

Abstract

A highly enantioselective aza-Friedel-Crafts (aza-F-C) reaction of cyclic trifluoromethyl ketimines and naphthols/phenols was developed with fluorenyl-substituted quinine-squaramide as the catalyst. This protocol enables direct access to biologically important chiral trifluoromethyl dihydroquinazolinones with up to 99% yields and up to 99% ee's.

Original language	English (US)
Pages (from-to)	5554-5557
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.5b02668
State	Published - Nov 20 2015
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A highly enantioselective aza-Friedel-Crafts (aza-F-C) reaction of cyclic trifluoromethyl ketimines and naphthols/phenols was developed with fluorenyl-substituted quinine-squaramide as the catalyst. This protocol enables direct access to biologically important chiral trifluoromethyl dihydroquinazolinones with up to 99% yields and up to 99% ee's.",

author = "Ding Zhou and Zheng Huang and Xueting Yu and Youxin Wang and Jian Li and Wei Wang and Hexin Xie",

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AU - Zhou, Ding

AU - Huang, Zheng

AU - Yu, Xueting

AU - Wang, Youxin

AU - Li, Jian

AU - Wang, Wei

AU - Xie, Hexin

PY - 2015/11/20

Y1 - 2015/11/20

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AB - A highly enantioselective aza-Friedel-Crafts (aza-F-C) reaction of cyclic trifluoromethyl ketimines and naphthols/phenols was developed with fluorenyl-substituted quinine-squaramide as the catalyst. This protocol enables direct access to biologically important chiral trifluoromethyl dihydroquinazolinones with up to 99% yields and up to 99% ee's.

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A Quinine-Squaramide Catalyzed Enantioselective Aza-Friedel-Crafts Reaction of Cyclic Trifluoromethyl Ketimines with Naphthols and Electron-Rich Phenols

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