Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines
Date
13/07/2015Author
Grant ID
EP/J018139/1
EP/J018139/1
EP/K031252/1
EP/K039210/1
Keywords
Metadata
Show full item recordAbstract
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
ISSN
0947-6539Type
Journal article
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.Collections
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