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Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids

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Slawin_2014_JOC_Isothiourea2_AM.pdf (1.504Mb)
Date
21/02/2014
Author
Morrill, Louis C.
Smith, Samuel M.
Slawin, Alexandra M. Z.
Smith, Andrew D.
Keywords
Bicyclic-Beta-Lactones
Enantioselective Gamma-Amination
Carbonylative 2+2 Cycloaddition
Catalyzed Aldol-Lactonization
Promoted Bis-Cyclizations
Acyl Transfer Catalyst
Delta-Lactones
Dyotropic Rearrangements
Efficient Synthesis
Ncal Reactions
QD Chemistry
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Abstract
Isothiourea HBTM-2.1 promotes the catalytic asymmetric alpha-functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.
Citation
Morrill , L C , Smith , S M , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids ' , Journal of Organic Chemistry , vol. 79 , no. 4 , pp. 1640-1655 . https://doi.org/10.1021/jo402591v
Publication
Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1021/jo402591v
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 To access the final edited and published work see http://dx.doi.org/10.1021/jo402591v
Description
This work is supported by funding from the Carnegie Trust for the Universities of Scotland (L.C.M.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013)/ERC Grant Agreement No. 279850.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/6073

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