Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides
Abstract
The isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangement of N,N-diallyl allylic ammonium ylides is explored as a key part of a route to free functionalised α-amino esters and piperidines. The [2,3]-sigmatropic rearrangement proceeds with excellent diastereo- and enantiocontrol (>95:5 dr, up to 97% ee), with the resultant N,N-diallyl α-amino esters undergoing either mono- or bis-N-allyl deprotection. Bis-N-allyl deprotection leads to free α-amino esters, while the mono-deprotection strategy has been utilized in the synthesis of a target functionalised piperidine.
Citation
West , T H , Spoehrle , S S M & Smith , A D 2017 , ' Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N , N -diallyl allylic ammonium ylides ' Tetrahedron , vol 73 , no. 29 , pp. 4138-4149 . DOI: 10.1016/j.tet.2017.01.062
Publication
Tetrahedron
Status
Peer reviewed
ISSN
0040-4020Type
Journal article
Rights
Copyright © 2017, Elsevier Ltd. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.tet.2017.01.062
Description
The research leading to these results (T.H.W.) has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007–2013)/E.R.C. grant agreement n° 279850 and the European Union (Marie Curie ITN “SubiCat” PITN-GA-2013-607044) (S. S. M. S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. The data underpinning this publication can be found at DOI: http://dx.doi.org/10.17630/f522b48d-ed02–42b3-a161-54687ea5af57Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.