Modular access to substituted azocanes via a rhodium-catalyzed cycloaddition-fragmentation strategy

Megan H. Shaw; Rosemary A. Croft; William G. Whittingham; John F. Bower

doi:10.1021/jacs.5b05215

Modular access to substituted azocanes via a rhodium-catalyzed cycloaddition-fragmentation strategy

Megan H. Shaw, Rosemary A. Croft, William G. Whittingham, John F. Bower

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

A short entry to substituted azocanes by a Rh-catalyzed cycloadditio −fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.

Original language	English
Pages (from-to)	8054-8057
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	25
DOIs	https://doi.org/10.1021/jacs.5b05215
Publication status	Published - 19 Jun 2015

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CatHet: New catalytic asymmetric strategies for N-heterocycle synthesis
Barry, L. S. (Principal Investigator)
1/04/15 → 31/03/20
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

Cite this

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title = "Modular access to substituted azocanes via a rhodium-catalyzed cycloaddition-fragmentation strategy",

abstract = "A short entry to substituted azocanes by a Rh-catalyzed cycloadditio −fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.",

author = "Shaw, {Megan H.} and Croft, {Rosemary A.} and Whittingham, {William G.} and Bower, {John F.}",

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doi = "10.1021/jacs.5b05215",

language = "English",

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T1 - Modular access to substituted azocanes via a rhodium-catalyzed cycloaddition-fragmentation strategy

AU - Shaw, Megan H.

AU - Croft, Rosemary A.

AU - Whittingham, William G.

AU - Bower, John F.

PY - 2015/6/19

Y1 - 2015/6/19

N2 - A short entry to substituted azocanes by a Rh-catalyzed cycloadditio −fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.

AB - A short entry to substituted azocanes by a Rh-catalyzed cycloadditio −fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.

U2 - 10.1021/jacs.5b05215

DO - 10.1021/jacs.5b05215

M3 - Article (Academic Journal)

C2 - 26090897

SN - 0002-7863

VL - 137

SP - 8054

EP - 8057

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 25

ER -

Modular access to substituted azocanes via a rhodium-catalyzed cycloaddition-fragmentation strategy

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CatHet: New catalytic asymmetric strategies for N-heterocycle synthesis

3-month Core Capability for Chemistry Research

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