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 . https://doi.org/10.1016/j.tet.2017.01.062
Publication
Tetrahedron
Status
Peer reviewed
ISSN
0040-4020Type
Journal article
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
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