The benzyne aza-claisen reaction

Alastair A. Cant; Guillaume H V Bertrand; Jaclyn L. Henderson; Lee Roberts; Michael F. Greaney

doi:10.1002/anie.200901410

The benzyne aza-claisen reaction

Alastair A. Cant, Guillaume H V Bertrand, Jaclyn L. Henderson, Lee Roberts, Michael F. Greaney

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

Abstract

Adding an aryne to a tertiary allylamine affords oallylaniline products of an aza-Claisen rearrangement. The aryne simultaneously provides the π component for the rearrangement and the quaternization event that lowers the activation energy for the sigmatropic shift. The reaction was applied to the synthesis of medium-ring benzannulated amines (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

Original language	English
Pages (from-to)	5199-5202
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	28
DOIs	https://doi.org/10.1002/anie.200901410
Publication status	Published - 29 Jun 2009

Keywords

Allylamines
Arynes
Aza-Claisen rearrangement
Medium-ring compounds

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title = "The benzyne aza-claisen reaction",

abstract = "Adding an aryne to a tertiary allylamine affords oallylaniline products of an aza-Claisen rearrangement. The aryne simultaneously provides the π component for the rearrangement and the quaternization event that lowers the activation energy for the sigmatropic shift. The reaction was applied to the synthesis of medium-ring benzannulated amines (see scheme). {\textcopyright} 2009 Wiley-VCH Verlag GmbH & Co. KGaA.",

keywords = "Allylamines, Arynes, Aza-Claisen rearrangement, Medium-ring compounds",

author = "Cant, {Alastair A.} and Bertrand, {Guillaume H V} and Henderson, {Jaclyn L.} and Lee Roberts and Greaney, {Michael F.}",

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T1 - The benzyne aza-claisen reaction

AU - Cant, Alastair A.

AU - Bertrand, Guillaume H V

AU - Henderson, Jaclyn L.

AU - Roberts, Lee

AU - Greaney, Michael F.

N1 - CAPLUS AN 2009:803417(Journal)

PY - 2009/6/29

Y1 - 2009/6/29

N2 - Adding an aryne to a tertiary allylamine affords oallylaniline products of an aza-Claisen rearrangement. The aryne simultaneously provides the π component for the rearrangement and the quaternization event that lowers the activation energy for the sigmatropic shift. The reaction was applied to the synthesis of medium-ring benzannulated amines (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

AB - Adding an aryne to a tertiary allylamine affords oallylaniline products of an aza-Claisen rearrangement. The aryne simultaneously provides the π component for the rearrangement and the quaternization event that lowers the activation energy for the sigmatropic shift. The reaction was applied to the synthesis of medium-ring benzannulated amines (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

KW - Allylamines

KW - Arynes

KW - Aza-Claisen rearrangement

KW - Medium-ring compounds

U2 - 10.1002/anie.200901410

DO - 10.1002/anie.200901410

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 28

ER -

The benzyne aza-claisen reaction

Abstract

Keywords

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