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

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Slawin_2014_JOC_Isothiourea3_AM.pdf (683.6Kb)
Date
07/02/2014
Author
Yeh, Pei-Pei
Daniels, David S. B.
Cordes, David B.
Slawin, Alexandra M. Z.
Smith, Andrew D.
Funder
EPSRC
The Royal Society
EPSRC
Grant ID
EP/J018139/1
UF090013
EP/J018139/1
Keywords
Bicyclic-Beta-Lactones
Catalyzed Aldol-Lactonization
Acyl Transfer Catalyst
Asymmetric-Synthesis
Dyotropic Rearrangements
Ncal Reactions
Keto Acids
3,5-dibromo-2-pyrone
QD Chemistry
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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.
Citation
Yeh , P-P , Daniels , D S B , Cordes , D B , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones ' , Organic Letters , vol. 16 , no. 3 , pp. 964-967 . https://doi.org/10.1021/ol403697h
Publication
Organic Letters
Status
Peer reviewed
DOI
https://doi.org/10.1021/ol403697h
ISSN
1523-7060
Type
Journal article
Rights
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
Description
The authors thank the Royal Society for a University Research Fellowship (ADS) and the EPSRC (EP/J018139/1, DSBD) for funding.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/6013

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