Solid-phase synthesis of pyrrolidines via 2-azaallyl anion cycloadditions with alkenes

✍ Scribed by William H. Pearson; Roger B. Clark

• Book ID: 104258120
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 224 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)10001-6

✦ Synopsis

The preparation of a variety of highly substituted pyrrolidines was achieved by solid-phase synthesis through the [2rts + 4~s] cycloaddition of 2-azaallyl anions with alkenes. Resin-bound aldehydes 2 were condensed with ct-arnino stannanes 3 to afford (2-azaallyl)stannanes 4. Transmetalation of 4 with n-BuLi in the presence of electron-rich alkenes followed by the addition of an electrophile provided the polymer-bound pyrrolidines 7. The free pyrrolidines 9-23 were obtained upon cleavage from the solid support.