Catalytic stereoselective [2,3]-rearrangement reactions

Thomas Henry West; Stephanie Suzanne Madeleine Spoehrle; Kevin Kasten; James Edward Taylor; Andrew David Smith

doi:10.1021/acscatal.5b02070

Catalytic stereoselective [2,3]-rearrangement reactions

Thomas Henry West, Stephanie Suzanne Madeleine Spoehrle, Kevin Kasten, James Edward Taylor, Andrew David Smith

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

126 Citations (Scopus)

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Abstract

[2,3]-Sigmatropic rearrangement processes of allylic ylides or their equivalents can be applied to a variety of different substrates and generate products of wide interest and applicability to organic synthesis. This review describes the development and applications of stereoselective [2,3]-rearrangement reactions in which a sub-stoichiometric amount of a catalyst is used in either the formation of the reactive intermediate or the [2,3]-rearrangement step itself.

Original language	English
Journal	ACS Catalysis
Volume	In press
Early online date	29 Oct 2015
DOIs	https://doi.org/10.1021/acscatal.5b02070
Publication status	Published - 2015

Keywords

Stereoselective catalysis
[2,3]-rearrangement
Allylic oxonium ylides
Allylic ammonium ylides
O-propargylic oximes
Allylic sulfoxides
Allylic N-oxides

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10.1021/acscatal.5b02070

Smith_2015_ACSC_Catalytic_AM
Copyright © 2015 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work see: https://dx.doi.org/10.1021/acscatal.5b02070
Accepted author manuscript, 1.07 MB

SUBICAT: SUBICAT
Kamer, P. C. J. (PI)
Marie Curie Fellowships
1/10/13 → 30/09/17
Project: Standard
Royal Society 516002.K501/kk: Academic Fellowship
Smith, A. D. (PI)
The Royal Society
1/10/05 → 30/09/10
Project: Fellowship

Cite this

@article{a48513981b1a4731ae2da38bb03a5a21,

title = "Catalytic stereoselective [2,3]-rearrangement reactions",

abstract = "[2,3]-Sigmatropic rearrangement processes of allylic ylides or their equivalents can be applied to a variety of different substrates and generate products of wide interest and applicability to organic synthesis. This review describes the development and applications of stereoselective [2,3]-rearrangement reactions in which a sub-stoichiometric amount of a catalyst is used in either the formation of the reactive intermediate or the [2,3]-rearrangement step itself. ",

keywords = "Stereoselective catalysis, [2,3]-rearrangement, Allylic oxonium ylides, Allylic ammonium ylides, O-propargylic oximes, Allylic sulfoxides, Allylic N-oxides",

author = "West, {Thomas Henry} and Spoehrle, {Stephanie Suzanne Madeleine} and Kevin Kasten and Taylor, {James Edward} and Smith, {Andrew David}",

note = "The authors thank the Royal Society for a University Research Fellowship (A.D.S.), the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-20013) ERC Grant Agreement No. 279850 (J.E.T., T.H.W., K.K.), and the European Union (Marie Curie ITN {\textquoteleft}SuBiCat{\textquoteright} PITN-GA-2013-607044) (S.S.M.S.) for financial support. ",

year = "2015",

doi = "10.1021/acscatal.5b02070",

language = "English",

volume = "In press",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society (ACS)",

}

TY - JOUR

T1 - Catalytic stereoselective [2,3]-rearrangement reactions

AU - West, Thomas Henry

AU - Spoehrle, Stephanie Suzanne Madeleine

AU - Kasten, Kevin

AU - Taylor, James Edward

AU - Smith, Andrew David

N1 - The authors thank the Royal Society for a University Research Fellowship (A.D.S.), the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-20013) ERC Grant Agreement No. 279850 (J.E.T., T.H.W., K.K.), and the European Union (Marie Curie ITN ‘SuBiCat’ PITN-GA-2013-607044) (S.S.M.S.) for financial support.

PY - 2015

Y1 - 2015

N2 - [2,3]-Sigmatropic rearrangement processes of allylic ylides or their equivalents can be applied to a variety of different substrates and generate products of wide interest and applicability to organic synthesis. This review describes the development and applications of stereoselective [2,3]-rearrangement reactions in which a sub-stoichiometric amount of a catalyst is used in either the formation of the reactive intermediate or the [2,3]-rearrangement step itself.

AB - [2,3]-Sigmatropic rearrangement processes of allylic ylides or their equivalents can be applied to a variety of different substrates and generate products of wide interest and applicability to organic synthesis. This review describes the development and applications of stereoselective [2,3]-rearrangement reactions in which a sub-stoichiometric amount of a catalyst is used in either the formation of the reactive intermediate or the [2,3]-rearrangement step itself.

KW - Stereoselective catalysis

KW - [2,3]-rearrangement

KW - Allylic oxonium ylides

KW - Allylic ammonium ylides

KW - O-propargylic oximes

KW - Allylic sulfoxides

KW - Allylic N-oxides

U2 - 10.1021/acscatal.5b02070

DO - 10.1021/acscatal.5b02070

M3 - Article

SN - 2155-5435

VL - In press

JO - ACS Catalysis

JF - ACS Catalysis

ER -

Catalytic stereoselective [2,3]-rearrangement reactions

Abstract

Keywords

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Projects

SUBICAT: SUBICAT

Royal Society 516002.K501/kk: Academic Fellowship

Cite this