title: The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.
abstract: Organic transformations that result in the formation of multiple covalent bonds within the same reaction are some of the most powerful tools in synthetic organic chemistry. Nitrosocarbonyl hetero-Diels-Alder (HDA) reactions allow for the simultaneous stereospecific introduction of carbon-nitrogen and carbon-oxygen bonds in one synthetic step, and provide direct access to 3,6-dihydro-1,2-oxazines. This Review describes the development of the nitrosocarbonyl HDA reaction and the utility of the resulting oxazine ring in the synthesis of a variety of important, biologically active molecules.
authors.affiliation: Chemspeed Technologies, Inc. 113 North Center Drive, North Brunswick, NJ 08906, USA.
authors.forename: Brian S
authors.initials: BS
authors.lastname: Bodnar
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D009603:Nitroso Compounds / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000475:Alkenes; D009603:Nitroso Compounds; D009705:Nucleosides; D010078:Oxazines