Organotin(IV) enamines as selective reagents: Coupling with α-halocarbonyls for synthesis of substituted pyrroles

✍ Scribed by Makoto Yasuda; Junji Morimoto; Ikuya Shibata; Akio Baba

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 123 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00598-4

✦ Synopsis

Effective coupling of tin enamines I and ct-haloaldehydes 2 gave 2,4-disubstituted pyrroles in high yields at room temperature even under aqueous conditions. The reaction with 2bromoaeetophenone gave 3,4-disubstituted pyrroles, while the addition of HMPA changed the selectivity to afford the 2,4-isomer predominantly (27 : 73).