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Isothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N-sulfonylaldimines

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Slawin_2014_JOC_Isothiourea_AM.pdf (1.660Mb)
Date
21/02/2014
Author
Smith, Siobhan R.
Douglas, James
Prevet, Hugues
Shapland, Peter
Slawin, Alexandra M. Z.
Smith, Andrew D.
Keywords
Human Cytomegalovirus Protease
Promoted Bis-Cyclizations
Acyl Transfer Catalyst
Pure Lithium Amides
Enantioselective Synthesis
Kinugasa Reaction
Aldol-Lactonization
Staudinger Reaction
Kinetic Resolution
Dyotropic Rearrangements
QD Chemistry
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Abstract
The isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereodefined 2,3-diaryl-β-amino esters (after ring-opening) and 3,4-diaryl-anti-β-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to excellent enantiocontrol. Deprotection of the N-tosyl substituent within the β-lactam framework was possible without racemization by treatment with SmI2.
Citation
Smith , S R , Douglas , J , Prevet , H , Shapland , P , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N -sulfonylaldimines ' , The Journal of Organic Chemistry , vol. 79 , no. 4 , pp. 1626-1639 . https://doi.org/10.1021/jo402590m
Publication
The Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1021/jo402590m
ISSN
0022-3263
Type
Journal article
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, 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/jo402590m
Description
This work is supported by a Royal Society for a University Research Fellowship and the EPSRC and GSK (Case Award) as well as by the European Research Council under the European Unionʼs 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/10023/6072

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