One-pot fluorination and organocatalytic Robinson annulation for asymmetric synthesis of mono- and difluorinated cyclohexenones

Xin Huang; Weizhao Zhao; Xiaofeng Zhang; Miao Liu; Stanley N.S. Vasconcelos; Wei Zhang

doi:10.3390/molecules23092251

One-pot fluorination and organocatalytic Robinson annulation for asymmetric synthesis of mono- and difluorinated cyclohexenones

Xin Huang
, Weizhao Zhao
, Xiaofeng Zhang
, Miao Liu
, Stanley N.S. Vasconcelos
, Wei Zhang

Chemistry

Zhejiang Normal University
University of Massachusetts Boston
Universidade de São Paulo

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

Abstract

A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.

Original language	English
Article number	2251
Journal	Molecules
Volume	23
Issue number	9
DOIs	https://doi.org/10.3390/molecules23092251
State	Published - Sep 4 2018

ASJC Scopus Subject Areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

Keywords

Cyclohexenone
Fluorination
Michael addition
Organocatalysis
Robinson annulation
Α-fluoro-β-keto ester

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10.3390/molecules23092251

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title = "One-pot fluorination and organocatalytic Robinson annulation for asymmetric synthesis of mono- and difluorinated cyclohexenones",

abstract = "A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99\% ee and 20:1 dr.",

keywords = "Cyclohexenone, Fluorination, Michael addition, Organocatalysis, Robinson annulation, Α-fluoro-β-keto ester",

author = "Xin Huang and Weizhao Zhao and Xiaofeng Zhang and Miao Liu and Vasconcelos, \{Stanley N.S.\} and Wei Zhang",

note = "Publisher Copyright: {\textcopyright} 2018 by the authors",

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month = sep,

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doi = "10.3390/molecules23092251",

language = "English",

volume = "23",

journal = "Molecules",

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T1 - One-pot fluorination and organocatalytic Robinson annulation for asymmetric synthesis of mono- and difluorinated cyclohexenones

AU - Huang, Xin

AU - Zhao, Weizhao

AU - Zhang, Xiaofeng

AU - Liu, Miao

AU - Vasconcelos, Stanley N.S.

AU - Zhang, Wei

PY - 2018/9/4

Y1 - 2018/9/4

N2 - A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.

AB - A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.

KW - Cyclohexenone

KW - Fluorination

KW - Michael addition

KW - Organocatalysis

KW - Robinson annulation

KW - Α-fluoro-β-keto ester

UR - https://www.scopus.com/pages/publications/85052861840

UR - https://www.scopus.com/pages/publications/85052861840#tab=citedBy

U2 - 10.3390/molecules23092251

DO - 10.3390/molecules23092251

M3 - Article

C2 - 30181479

AN - SCOPUS:85052861840

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 9

M1 - 2251

ER -

One-pot fluorination and organocatalytic Robinson annulation for asymmetric synthesis of mono- and difluorinated cyclohexenones

Abstract

ASJC Scopus Subject Areas

Keywords

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