Asymmetric 1,3-dipolar cycloadditions of acrylamides

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MK_AsymmetricAV2010.pdf(3.48 MB)
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Date
2009
Authors
Kissane, Marie
Maguire, Anita R.
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RSC Publishing
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Abstract
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).
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Asymmetric 1,3-dipolar cycloadditions , Chiral acrylamides , Stereocontrol , Regioselectivity , Nitrile oxides , Nitrones , Diazoalkanes , Azomethine ylides , Stereoselectivity
Citation
KISSANE, M. & MAGUIRE, A. R. 2010. Asymmetric 1,3-dipolar cycloadditions of acrylamides. Chemical Society Reviews, 39, 845-883. doi:10.1039/B909358N
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©2010, The Authors. Exclusive licence to publish RSC Publishing.