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alpha-Ketophosphonates as ester surrogates : isothiourea-catalyzed asymmetric diester and lactone synthesis

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Date
02/05/2014
Author
Smith, Siobhan R.
Leckie, Stuart M.
Holmes, Reuben
Douglas, James
Fallan, Charlene
Shapland, Peter
Pryde, David
Slawin, Alexandra M. Z.
Smith, Andrew D.
Funder
The Royal Society
Grant ID
UF090013
Keywords
Bicyclic-beta-lactones
Bis(oxazolinyl)pyridine-scandium(III) triflate complexes
Friedel-Crafts alkylations
Acyl transfer catalyst
Diels-Alder reactions
Aldol-Lactonization
Dyotropic Rearrangements
Keto Acids
Organocatalysis
Michael
QD Chemistry
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Abstract
Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or enantioenriched functionalized diesters upon ring-opening.
Citation
Smith , S R , Leckie , S M , Holmes , R , Douglas , J , Fallan , C , Shapland , P , Pryde , D , Slawin , A M Z & Smith , A D 2014 , ' alpha-Ketophosphonates as ester surrogates : isothiourea-catalyzed asymmetric diester and lactone synthesis ' , Organic Letters , vol. 16 , no. 9 , pp. 2506-2509 . https://doi.org/10.1021/ol500873s
Publication
Organic Letters
Status
Peer reviewed
DOI
https://doi.org/10.1021/ol500873s
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/ol500873s
Description
This work is in part supported by the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/6480

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