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All‐Carbon Intramolecular Conjugate Displacement Reactions: An Effective Route to Carbocycles
Author(s) -
Prabhudas Bodhuri,
Clive Derrick L. J.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200703022
Subject(s) - intramolecular force , carbanion , chemistry , conjugate , allylic rearrangement , nucleophile , sn2 reaction , carbon fibers , displacement (psychology) , leaving group , medicinal chemistry , nucleophilic substitution , stereochemistry , organic chemistry , catalysis , materials science , mathematics , psychology , mathematical analysis , composite number , composite material , psychotherapist
Working together : Synergy between Michael addition and S N 2′ displacement allows stabilized carbanions or the nucleophilic carbon atoms of enamines to undergo intramolecular addition to an α,β‐unsaturated ester unit bearing an allylic leaving group to generate unsaturated carbocycles (see scheme). The starting esters are available by a selenium‐based alternative to the classical Baylis–Hillman reaction, and complex structures can be assembled.