Fluorine containing cyclopropanes: synthesis of aryl substituted all-cis 1,2,3-trifluorocylopropanes, a facially polar motif

Zeguo Fang; David B. Cordes; Alexandra M. Z. Slawin; David O'Hagan

doi:10.1039/C9CC05749H

Fluorine containing cyclopropanes: synthesis of aryl substituted all-cis 1,2,3-trifluorocylopropanes, a facially polar motif

Zeguo Fang, David B. Cordes, Alexandra M. Z. Slawin, David O'Hagan

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

Abstract

The synthesis of substituted all-cis-1,2,3-trifluorocylopropanes are described for the first time. The three fluorines located on each of the cyclopropyl carbons with a stereochemistry where they are all on the same face of the cyclopropane, imparts a significant polarity to the molecule, and the inherent conformational rigidity and lowering of Log P makes this motif attractive for exploration as a substituent for pharmaceuticals and agrochemicals research.

Original language	English
Pages (from-to)	10539-10542
Journal	Chemical Communications
Volume	55
Issue number	71
Early online date	9 Aug 2019
DOIs	https://doi.org/10.1039/C9CC05749H
Publication status	Published - 14 Sept 2019

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10.1039/C9CC05749H

O'Hagan_2019_CC_Cyclopropanes_AAM
Copyright © 2019 The Author(s). This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1039/C9CC05749H
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Cite this

@article{1242827033e747e2ba329fade2c284b1,

title = "Fluorine containing cyclopropanes: synthesis of aryl substituted all-cis 1,2,3-trifluorocylopropanes, a facially polar motif",

abstract = "The synthesis of substituted all-cis-1,2,3-trifluorocylopropanes are described for the first time. The three fluorines located on each of the cyclopropyl carbons with a stereochemistry where they are all on the same face of the cyclopropane, imparts a significant polarity to the molecule, and the inherent conformational rigidity and lowering of Log P makes this motif attractive for exploration as a substituent for pharmaceuticals and agrochemicals research.",

author = "Zeguo Fang and Cordes, \{David B.\} and Slawin, \{Alexandra M. Z.\} and David O'Hagan",

note = "We thank the EPSRC for financial support (GR: EP/R013799/1) and we are grateful to the Chinese Scholarship Council (CSC) for Ph.D Studentship support (ZF).",

year = "2019",

month = sep,

day = "14",

doi = "10.1039/C9CC05749H",

language = "English",

volume = "55",

pages = "10539--10542",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "71",

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TY - JOUR

T1 - Fluorine containing cyclopropanes

T2 - synthesis of aryl substituted all-cis 1,2,3-trifluorocylopropanes, a facially polar motif

AU - Fang, Zeguo

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - O'Hagan, David

N1 - We thank the EPSRC for financial support (GR: EP/R013799/1) and we are grateful to the Chinese Scholarship Council (CSC) for Ph.D Studentship support (ZF).

PY - 2019/9/14

Y1 - 2019/9/14

N2 - The synthesis of substituted all-cis-1,2,3-trifluorocylopropanes are described for the first time. The three fluorines located on each of the cyclopropyl carbons with a stereochemistry where they are all on the same face of the cyclopropane, imparts a significant polarity to the molecule, and the inherent conformational rigidity and lowering of Log P makes this motif attractive for exploration as a substituent for pharmaceuticals and agrochemicals research.

AB - The synthesis of substituted all-cis-1,2,3-trifluorocylopropanes are described for the first time. The three fluorines located on each of the cyclopropyl carbons with a stereochemistry where they are all on the same face of the cyclopropane, imparts a significant polarity to the molecule, and the inherent conformational rigidity and lowering of Log P makes this motif attractive for exploration as a substituent for pharmaceuticals and agrochemicals research.

UR - https://www.scopus.com/pages/publications/85071618639

U2 - 10.1039/C9CC05749H

DO - 10.1039/C9CC05749H

M3 - Article

SN - 1359-7345

VL - 55

SP - 10539

EP - 10542

JO - Chemical Communications

JF - Chemical Communications

IS - 71

ER -

Fluorine containing cyclopropanes: synthesis of aryl substituted all-cis 1,2,3-trifluorocylopropanes, a facially polar motif

Abstract

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Partially fluorinated alkyl motifs: Partially fluorinated alkyl motifs for pharmaceuticals and agrochemicals research