Asymmetric 1,3-dipolar cycloadditions of acrylamides

Marie Kissane; Anita R. Maguire

doi:10.1039/B909358N

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Chemical Society Reviews

Issue 2, 2010

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Critical Review

Asymmetric 1,3-dipolar cycloadditions of acrylamides

Marie Kissane^a and Anita R. Maguire*^b

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Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland

Department of Chemistry & School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
E-mail: a.maguire@ucc.ie ;
Fax: +353 21 4274097 ;
Tel: +353 21 4901693

Chem. Soc. Rev., 2010,39, 845-883

DOI: 10.1039/B909358N
Received 24 Jul 2009, First published online 07 Dec 2009

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Abstract
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This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references).

Abstract from Methods in Organic Synthesis 2010

A review, with 215 references, of asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with an emphasis on the rationale for the observed stereocontrol.

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