Three step synthesis of single diastereoisomers of the vicinal trifluoro motif

Vincent A. Brunet; Alexandra M. Z. Slawin; David O'Hagan

doi:10.3762/bjoc.5.61

Three step synthesis of single diastereoisomers of the vicinal trifluoro motif

Vincent A. Brunet, Alexandra M. Z. Slawin, David O'Hagan

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

Abstract

A three step route to single diastereoisomers of the vicinal trifluoromethyl motif is described. The route starts from either syn- or anti-alpha,beta-epoxy alcohols and takes a direct approach in that each of the three steps introduces a fluorine atom in a regio- and stereospecific manner. Starting from either the syn- or the anti-alpha,beta-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy.

Original language	English
Article number	61
Number of pages	9
Journal	Beilstein Journal of Organic Chemistry
Volume	5
DOIs	https://doi.org/10.3762/bjoc.5.61
Publication status	Published - 5 Nov 2009

Keywords

C-F bond
organo-fluorine chemistry
stereospecific fluorination
vicinal trifluoro motif
Kinetic resolution
Hydrogen-fluoride
Fluorination
Chemistry
Epoxides
Bond

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10.3762/bjoc.5.61

OHagan2009BeilsteinJOrgChem5 61
© 2009 Brunet et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
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title = "Three step synthesis of single diastereoisomers of the vicinal trifluoro motif",

abstract = "A three step route to single diastereoisomers of the vicinal trifluoromethyl motif is described. The route starts from either syn- or anti-alpha,beta-epoxy alcohols and takes a direct approach in that each of the three steps introduces a fluorine atom in a regio- and stereospecific manner. Starting from either the syn- or the anti-alpha,beta-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy.",

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year = "2009",

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AU - Brunet, Vincent A.

AU - Slawin, Alexandra M. Z.

AU - O'Hagan, David

PY - 2009/11/5

Y1 - 2009/11/5

N2 - A three step route to single diastereoisomers of the vicinal trifluoromethyl motif is described. The route starts from either syn- or anti-alpha,beta-epoxy alcohols and takes a direct approach in that each of the three steps introduces a fluorine atom in a regio- and stereospecific manner. Starting from either the syn- or the anti-alpha,beta-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy.

AB - A three step route to single diastereoisomers of the vicinal trifluoromethyl motif is described. The route starts from either syn- or anti-alpha,beta-epoxy alcohols and takes a direct approach in that each of the three steps introduces a fluorine atom in a regio- and stereospecific manner. Starting from either the syn- or the anti-alpha,beta-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy.

KW - C-F bond

KW - organo-fluorine chemistry

KW - stereospecific fluorination

KW - vicinal trifluoro motif

KW - Kinetic resolution

KW - Hydrogen-fluoride

KW - Fluorination

KW - Chemistry

KW - Epoxides

KW - Bond

U2 - 10.3762/bjoc.5.61

DO - 10.3762/bjoc.5.61

M3 - Article

SN - 1860-5397

VL - 5

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

M1 - 61

ER -

Three step synthesis of single diastereoisomers of the vicinal trifluoro motif

Abstract

Keywords

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