An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides
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Benzotetramisole promotes the catalytic asymmetric [2,,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-alpha-amino acid derivatives with excellent diastereo- and enantioselectivity (up to >95:5 dr; up to >99% ee).
West , T H , Daniels , D S B , Slawin , A M Z & Smith , A D 2014 , ' An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides ' Journal of the American Chemical Society , vol 136 , no. 12 , pp. 4476-4479 . DOI: 10.1021/ja500758n
Journal of the American Chemical Society
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/ja500758n.
We thank the Royal Society for a URF (A.D.S.), the ERC under the European Union’s Seventh Framework Programme (FP7/2007-2013, grant agreement no. 279850) (T.H.W.), and EPSRC grant No. EP/J018139/1 (D.S.B.D.) for funding.