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The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses
Author(s) -
Bodnar Brian S.,
Miller Marvin J.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201005764
Subject(s) - organic synthesis , chemistry , diels–alder reaction , covalent bond , stereospecificity , ring (chemistry) , organic molecules , oxazines , organic chemistry , combinatorial chemistry , organic reaction , carbon fibers , nitrogen , molecule , catalysis , materials science , composite number , composite material
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.