First example of a third generation nitrone cycloaddition

✍ Scribed by Pedro de March; Marta Figueredo; Josep Font; Sergio Milán; Angel Alvarez-Larena; Juan F. Piniella; Elies Molins

• Book ID: 104207517
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 565 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01177-5

✦ Synopsis

Compounds 5 and 6, derived from the cycloadditions of a nitrone to ot,l~-unsaturated lactones, were oxidized with m-chloroperbenzoic acid affording regiospecifically aldonitrones, 8 and 14, respectively. These second generation nitrones were reacted with several dipolarophiles yielding cycloadduets 9-13, 15, and 16. A repeated sequence of oxidation-cycloaddition applied to compound 12 allowed the isolation of the first example of a tlfird generation cycloadduct, 17. During this work a series of new highly functionalized pyrrolidines have been prepared.