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

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

doi:10.1021/ja500758n

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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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).

Original language	English
Pages (from-to)	4476-4479
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	12
Early online date	3 Mar 2014
DOIs	https://doi.org/10.1021/ja500758n
Publication status	Published - 26 Mar 2014

Keywords

Ketene-Forming Eliminations
Amino-Acid Derivatives
Acyl Transfer Catalyst
One-Pot Synthesis
Kinetic Resolution
Organocatalytic Activation
Aryl Phenylacetates
Rearrangement
Esters
Benzotetramisole

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10.1021/ja500758n

West_2014_JACS_Isothiourea
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.
Accepted author manuscript, 343 KB

Cite this

@article{126c4796b7bf43b08ad197749b2ab84c,

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

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).",

keywords = "Ketene-Forming Eliminations, Amino-Acid Derivatives, Acyl Transfer Catalyst, One-Pot Synthesis, Kinetic Resolution, Organocatalytic Activation, Aryl Phenylacetates, Rearrangement, Esters, Benzotetramisole",

author = "West, {Thomas H.} and Daniels, {David S. B.} and Slawin, {Alexandra M. Z.} and Smith, {Andrew D.}",

note = "We thank the Royal Society for a URF (A.D.S.), the ERC under the European Union{\textquoteright}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.",

year = "2014",

month = mar,

day = "26",

doi = "10.1021/ja500758n",

language = "English",

volume = "136",

pages = "4476--4479",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society (ACS)",

number = "12",

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TY - JOUR

T1 - An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides

AU - West, Thomas H.

AU - Daniels, David S. B.

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

N1 - 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.

PY - 2014/3/26

Y1 - 2014/3/26

N2 - 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).

AB - 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).

KW - Ketene-Forming Eliminations

KW - Amino-Acid Derivatives

KW - Acyl Transfer Catalyst

KW - One-Pot Synthesis

KW - Kinetic Resolution

KW - Organocatalytic Activation

KW - Aryl Phenylacetates

KW - Rearrangement

KW - Esters

KW - Benzotetramisole

UR - http://pubs.acs.org/doi/suppl/10.1021/ja500758n

U2 - 10.1021/ja500758n

DO - 10.1021/ja500758n

M3 - Article

SN - 0002-7863

VL - 136

SP - 4476

EP - 4479

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 12

ER -

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

Abstract

Keywords

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Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - Cabranes ans Lewis Bases as Organocatalysts Synthetic Applications

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - Cabranes ans Lewis Bases as Organocatalysts Synthetic Applications

Cite this