A radical cyclization route to pyrrolidines based on conjugate addition to electron deficient phenylselenenylalkenes

✍ Scribed by Stefan Berlin; Lars Engman

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 133 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00446-9

✦ Synopsis

α-Phenylselenenyl-α,β-unsaturated esters, amides, ketones, nitriles and sulfones were prepared by zinc chloride promoted chloroselenation/dehydrochlorination of the corresponding α,β-unsaturated compounds. After Michael addition of allyl or propargylamine and triethylborane initiated reductive radical cyclization in the presence of tris(trimethylsilyl)silane, pyrrolidine and dihydropyrrole derivatives, respectively, were obtained.