A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen

Gavin J. Harkness; Matthew Lee Clarke

doi:10.1002/ejoc.201700791

A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen

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

Abstract

A highly enantioselective synthesis of (S)-Flurbiprofen methyl ester in two steps from commercially available 4-bromo-2-fluoro-1,1'-biphenyl is shown. [PdCl2((S)-Xylyl-Phanephos)] catalyst is used to accomplish both Grignard cross-coupling and the highly enantioselective intermolecular methoxycarbonylation reaction.

Original language	English
Pages (from-to)	4859-4863
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	32
Early online date	31 Aug 2017
DOIs	https://doi.org/10.1002/ejoc.201700791
Publication status	Published - 1 Sept 2017

Keywords

Palladium
Asymmetric catalysis
Carbonylation
Hydroesterification
Hydroxycarbonylation

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10.1002/ejoc.201700791

Harkness_2017_EJOC_ConciseSynthesis_AAM
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 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 as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/ejoc.201700791
Accepted author manuscript, 1.65 MB

Enantioselective Carbonylations: New Insights New Catalysts and New Processes using Enantioselective Carbonylations
Clarke, M. (PI) & Buehl, M. (CoI)
EPSRC
1/09/14 → 30/11/17
Project: Standard

A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen. (dataset)
Harkness, G. J. (Creator) & Clarke, M. L. (Creator), University of St Andrews, 2017
DOI: 10.17630/9aa92a84-6fa4-4f72-92be-1d409a5f2c6b
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title = "A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen",

abstract = "A highly enantioselective synthesis of (S)-Flurbiprofen methyl ester in two steps from commercially available 4-bromo-2-fluoro-1,1'-biphenyl is shown. [PdCl2((S)-Xylyl-Phanephos)] catalyst is used to accomplish both Grignard cross-coupling and the highly enantioselective intermolecular methoxycarbonylation reaction.",

keywords = "Palladium, Asymmetric catalysis, Carbonylation, Hydroesterification, Hydroxycarbonylation",

author = "Harkness, {Gavin J.} and Clarke, {Matthew Lee}",

note = "The authors thank the EPSRC for funding for this programme from EP/MC038868/1 and via the DTG.",

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doi = "10.1002/ejoc.201700791",

language = "English",

volume = "2017",

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journal = "European Journal of Organic Chemistry",

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TY - JOUR

T1 - A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen

AU - Harkness, Gavin J.

AU - Clarke, Matthew Lee

N1 - The authors thank the EPSRC for funding for this programme from EP/MC038868/1 and via the DTG.

PY - 2017/9/1

Y1 - 2017/9/1

N2 - A highly enantioselective synthesis of (S)-Flurbiprofen methyl ester in two steps from commercially available 4-bromo-2-fluoro-1,1'-biphenyl is shown. [PdCl2((S)-Xylyl-Phanephos)] catalyst is used to accomplish both Grignard cross-coupling and the highly enantioselective intermolecular methoxycarbonylation reaction.

AB - A highly enantioselective synthesis of (S)-Flurbiprofen methyl ester in two steps from commercially available 4-bromo-2-fluoro-1,1'-biphenyl is shown. [PdCl2((S)-Xylyl-Phanephos)] catalyst is used to accomplish both Grignard cross-coupling and the highly enantioselective intermolecular methoxycarbonylation reaction.

KW - Palladium

KW - Asymmetric catalysis

KW - Carbonylation

KW - Hydroesterification

KW - Hydroxycarbonylation

U2 - 10.1002/ejoc.201700791

DO - 10.1002/ejoc.201700791

M3 - Article

SN - 1099-0690

VL - 2017

SP - 4859

EP - 4863

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 32

ER -

A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen

Abstract

Keywords

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Projects

Enantioselective Carbonylations: New Insights New Catalysts and New Processes using Enantioselective Carbonylations

Datasets

A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen. (dataset)

Cite this