Biomaterial Database

Asymmetric 1,3-dipolar cycloadditions of acrylamides. 2010

Marie Kissane, and Anita R Maguire

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

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).

UI	MeSH Term	Description	Entries
D009570	Nitriles	Organic compounds containing the -CN radical. The concept is distinguished from CYANIDES, which denotes inorganic salts of HYDROGEN CYANIDE.	Nitrile
D009589	Nitrogen Oxides	Inorganic oxides that contain nitrogen.	Nitrogen Oxide,Oxide, Nitrogen,Oxides, Nitrogen
D003979	Diazonium Compounds	Azo compounds consisting of an aryl or alkyl group that is joined through two nitrogen atoms to an anion (R-N2+X-).	Compounds, Diazonium
D006571	Heterocyclic Compounds	Cyclic compounds that include atoms other than carbon in their ring structure.	Heterocyclic Compound,Compound, Heterocyclic,Compounds, Heterocyclic
D000178	Acrylamides	Colorless, odorless crystals that are used extensively in research laboratories for the preparation of polyacrylamide gels for electrophoresis and in organic synthesis, and polymerization. Some of its polymers are used in sewage and wastewater treatment, permanent press fabrics, and as soil conditioning agents.
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer