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Intramolecular Addition of γ‐Chloro Carbanions to Electrophilic Groups: Synthesis of Tricyclic Tetrahydrofurans, Pyrrolidines, and Cyclopentanes
Author(s) -
Wojtasiewicz Anna,
Barbasiewicz Michał,
Mąkosza Mieczysław
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901131
Subject(s) - chemistry , carbanion , intramolecular force , cyclopentane , electrophile , tricyclic , medicinal chemistry , pyrrolidine , tetrahydrofuran , cyclopentanes , aldol reaction , electrophilic substitution , ring (chemistry) , aldol condensation , stereochemistry , organic chemistry , catalysis , solvent
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.