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Enzyme‐like Control of Carbocation Deprotonation Regioselectivity in Supramolecular Catalysis of the Nazarov Cyclization
Author(s) -
Hastings Courtney J.,
Backlund Mikael P.,
Bergman Robert G.,
Raymond Kenneth N.
Publication year - 2011
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.201105325
Subject(s) - regioselectivity , deprotonation , carbocation , chemistry , supramolecular chemistry , kinetic control , catalysis , selectivity , ligand (biochemistry) , stereochemistry , photochemistry , organic chemistry , molecule , ion , biochemistry , receptor
The kinetically controlled, regioselective deprotonation of cyclopentenyl cations is mediated by encapsulation within a metal–ligand assembly. The regiochemistry of the deprotonation step determines which one of two possible products is formed. Moreover, subtle differences in the stereochemistry of the encapsulated cation switch the selectivity of this process (see scheme).