The Nitrosocarbonyl Hetero-Diels–Alder Reaction as a Useful Tool for Organic Syntheses

✍ Scribed by Dr. Brian S. Bodnar; Prof. Dr. Marvin J. Miller

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 928 KB
• Volume: 50
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.201005764

✦ Synopsis

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.