An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides

West, Thomas H.; Daniels, David S. B.; Slawin, Alexandra M. Z.; Smith, Andrew D.

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dc.contributor.author	West, Thomas H.
dc.contributor.author	Daniels, David S. B.
dc.contributor.author	Slawin, Alexandra M. Z.
dc.contributor.author	Smith, Andrew D.
dc.date.accessioned	2015-03-03T00:01:49Z
dc.date.available	2015-03-03T00:01:49Z
dc.date.issued	2014-03-26
dc.identifier	116646440
dc.identifier	126c4796-b7bf-43b0-8ad1-97749b2ab84c
dc.identifier	000333551800008
dc.identifier	84897081812
dc.identifier	000333551800008
dc.identifier.citation	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 . https://doi.org/10.1021/ja500758n	en
dc.identifier.issn	0002-7863
dc.identifier.other	ORCID: /0000-0002-2104-7313/work/36567511
dc.identifier.other	ORCID: /0000-0002-9527-6418/work/56861601
dc.identifier.uri	https://hdl.handle.net/10023/6153
dc.description	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.	en
dc.description.abstract	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).
dc.format.extent	4
dc.format.extent	351496
dc.language.iso	eng
dc.relation.ispartof	Journal of the American Chemical Society	en
dc.subject	Ketene-Forming Eliminations	en
dc.subject	Amino-Acid Derivatives	en
dc.subject	Acyl Transfer Catalyst	en
dc.subject	One-Pot Synthesis	en
dc.subject	Kinetic Resolution	en
dc.subject	Organocatalytic Activation	en
dc.subject	Aryl Phenylacetates	en
dc.subject	Rearrangement	en
dc.subject	Esters	en
dc.subject	Benzotetramisole	en
dc.subject	QD Chemistry	en
dc.subject.lcc	QD	en
dc.title	An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides	en
dc.type	Journal article	en
dc.contributor.sponsor	EPSRC	en
dc.contributor.sponsor	The Royal Society	en
dc.contributor.sponsor	EPSRC	en
dc.contributor.institution	University of St Andrews. School of Chemistry	en
dc.contributor.institution	University of St Andrews. EaSTCHEM	en
dc.contributor.institution	University of St Andrews. Biomedical Sciences Research Complex	en
dc.identifier.doi	10.1021/ja500758n
dc.description.status	Peer reviewed	en
dc.date.embargoedUntil	2015-03-03
dc.identifier.url	http://pubs.acs.org/doi/suppl/10.1021/ja500758n	en
dc.identifier.grantnumber	EP/J018139/1	en
dc.identifier.grantnumber	UF090013	en
dc.identifier.grantnumber	EP/J018139/1	en

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