Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones

Pei-Pei Yeh; David S. B. Daniels; David B. Cordes; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1021/ol403697h

Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones

Pei-Pei Yeh, David S. B. Daniels, David B. Cordes, Alexandra M. Z. Slawin, Andrew D. Smith^*

^*Corresponding author for this work

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

Abstract

A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.

Original language	English
Pages (from-to)	964-967
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	3
Early online date	16 Jan 2014
DOIs	https://doi.org/10.1021/ol403697h
Publication status	Published - 7 Feb 2014

Keywords

Bicyclic-Beta-Lactones
Catalyzed Aldol-Lactonization
Acyl Transfer Catalyst
Asymmetric-Synthesis
Dyotropic Rearrangements
Ncal Reactions
Keto Acids
3,5-dibromo-2-pyrone

Access to Document

10.1021/ol403697h

Slawin_2014_JOC_Isothiourea3_AM
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © 2014 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol403697h
Accepted author manuscript, 684 KB

Clean catalysis for sustainable develop: Clean catalysis for sustainable development
Kamer, P. C. J. (PI)
EPSRC
1/11/12 → 31/10/17
Project: Standard
Clean catalysis for sustainable develop: Clean catalysis for sustainable development
Smith, A. D. (PI)
EPSRC
1/11/12 → 31/10/17
Project: Standard
RS Uni Research Fellowship Renewal 2010: University Research Fellowship - Cabranes ans Lewis Bases as Organocatalysts Synthetic Applications
Smith, A. D. (PI)
The Royal Society
1/10/10 → 30/09/13
Project: Fellowship

Cite this

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title = "Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones",

abstract = "A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.",

keywords = "Bicyclic-Beta-Lactones, Catalyzed Aldol-Lactonization, Acyl Transfer Catalyst, Asymmetric-Synthesis, Dyotropic Rearrangements, Ncal Reactions, Keto Acids, 3,5-dibromo-2-pyrone",

author = "Pei-Pei Yeh and Daniels, {David S. B.} and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Smith, {Andrew D.}",

note = "The authors thank the Royal Society for a University Research Fellowship (ADS) and the EPSRC (EP/J018139/1, DSBD) for funding.",

year = "2014",

month = feb,

day = "7",

doi = "10.1021/ol403697h",

language = "English",

volume = "16",

pages = "964--967",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "3",

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TY - JOUR

T1 - Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones

AU - Yeh, Pei-Pei

AU - Daniels, David S. B.

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

N1 - The authors thank the Royal Society for a University Research Fellowship (ADS) and the EPSRC (EP/J018139/1, DSBD) for funding.

PY - 2014/2/7

Y1 - 2014/2/7

N2 - A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.

AB - A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.

KW - Bicyclic-Beta-Lactones

KW - Catalyzed Aldol-Lactonization

KW - Acyl Transfer Catalyst

KW - Asymmetric-Synthesis

KW - Dyotropic Rearrangements

KW - Ncal Reactions

KW - Keto Acids

KW - 3,5-dibromo-2-pyrone

U2 - 10.1021/ol403697h

DO - 10.1021/ol403697h

M3 - Article

SN - 1523-7060

VL - 16

SP - 964

EP - 967

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones

Abstract

Keywords

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Projects

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - Cabranes ans Lewis Bases as Organocatalysts Synthetic Applications

Cite this