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Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines

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Date
13/07/2015
Author
Smith, Siobhan Rose
Fallan, Charlene
Taylor, James Edward
McLennan, Ross Sinclair
Daniels, David Sydney Bernard
Morrill, Louis Christian
Slawin, Alexandra Martha Zoya
Smith, Andrew David
Keywords
Organocatalysis
Nitrogen heterocycles
Oxygen heterocycles
Asymmetric synthesis
QD Chemistry
DAS
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Abstract
A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high dr, yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.
Citation
Smith , S R , Fallan , C , Taylor , J E , McLennan , R S , Daniels , D S B , Morrill , L C , Slawin , A M Z & Smith , A D 2015 , ' Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines ' , Chemistry - A European Journal , vol. 21 , no. 29 , pp. 10530–10536 . https://doi.org/10.1002/chem.201501271
Publication
Chemistry - A European Journal
Status
Peer reviewed
DOI
https://doi.org/10.1002/chem.201501271
ISSN
0947-6539
Type
Journal article
Rights
© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Description
The authors thank the Royal Society for a University Research Fellowship (A.D.S.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007—2013), ERC Grant Agreement No. 279850 (C.F. and J.E.T.), GSK (CASE award to S.R.S.) and EPSRC grant No. EP/J018139/1 (D.S.B.D.) for funding.
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  • University of St Andrews Research
URL
http://onlinelibrary.wiley.com/doi/10.1002/chem.201501271/suppinfo
URI
http://hdl.handle.net/10023/7021

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