Optically Pure 3,6-Dioxazocan-2-one Derivatives by Intramolecular Cycloaddition of Azidoformates and their Opening to Substituted α-Amino Ketones

✍ Scribed by Marco de Santis; Stefania Fioravanti; Lucio Pellacani; Paolo A. Tardella

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 216 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199911)1999:11<2709::aid-ejoc2709>3.0.co;2-h

✦ Synopsis

Azidoformates derived from chiral enol ethers, when hydrolysis of 7 gives a single derivative of 2-aminocyclohexanone. irradiated, give 3,6-dioxazocan-2-one derivatives 7 by a highly diastereoselective intramolecular cycloaddition. The [a] Dipartimento di Chimica dellЈUniversita `di Roma "La Sapienza", chain ending with an azido function it is possible to obtain