Intramolecular Addition of γ-Chloro Carbanions to Electrophilic Groups: Synthesis of Tricyclic Tetrahydrofurans, Pyrrolidines, and Cyclopentanes

✍ Scribed by Anna Wojtasiewicz; Michał Barbasiewicz; Mieczysław Mąkosza

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 283 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200901131

✦ Synopsis

Abstract

Carbanions of 3‐chloropropyl phenyl sulfones containing electrophilic groups such as carbonyl and imino groups in the ortho position of the phenyl ring add intramolecularly to these groups to give aldol‐type anions. These anions undergo intramolecular 1,5‐substitution of chlorine to give tricyclic derivatives of tetrahydrofuran, pyrrolidine, and cyclopentane.