Asymmetric 1,3-dipolar cycloadditions of acrylamides.
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).
Kissane
Marie
M
Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland.
Maguire
Anita R
AR
D000178:Acrylamides / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry; D013237:Stereoisomerism
D000178:Acrylamides; D003979:Diazonium Compounds; D006571:Heterocyclic Compounds; D009570:Nitriles; D009589:Nitrogen Oxides; C015388:nitrones