Preparation of 2,2,6-trisubstituted 7-oxa-1-azabicyclo[2.2.1]heptanes from 4-nitro-1-butene derivatives. A route to 2,2,6-trisubstituted-4-hydroxypiperidines

✍ Scribed by Anna Budzińska; Maria Bukowska; Wojciech Sas

• Book ID: 104260401
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 272 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02357-0

✦ Synopsis

4-Nitro-l-butene derivatives 2 readily available f~om the palladium(0)-catalyzed C-allylation of nitroalkanes were converted into 7-oxa-l-azabicyclo[2.2.1]heptane derivatives 5 in three easy steps including an intramolecular 1,3-dipolar cycloaddition reaction of N-(3-alkenyl)nitrones.

The palladium catalyzed hydrogenolysis of the compounds 5 afforded 2,2,6-trisubstituted-4-hydroxypiperidines. The oxidation of 5 by 3 equiv, of m-ctdoroperbenzoic acid (MCPBA) gave acyclic 13-hydroxy-~i-nitroketones 9 in high yield.