Enzyme-like control of carbocation deprotonation regioselectivity in supramolecular catalysis of the nazarov cyclization

Courtney J. Hastings; Mikael P. Backlund; Robert G. Bergman; Kenneth N. Raymond

doi:10.1002/anie.201105325

Enzyme-like control of carbocation deprotonation regioselectivity in supramolecular catalysis of the nazarov cyclization

Courtney J. Hastings, Mikael P. Backlund, Robert G. Bergman, Kenneth N. Raymond

Research output: Contribution to journal › Article › peer-review

Abstract

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).

Original language	English (US)
Pages (from-to)	10570-10573
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	45
DOIs	https://doi.org/10.1002/anie.201105325
State	Published - Nov 4 2011
Externally published	Yes

Keywords

cage compounds
carbocations
electrocyclic reactions
homogeneous catalysis
supramolecular chemistry

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Online availability

10.1002/anie.201105325

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AU - Raymond, Kenneth N.

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AB - 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).

KW - cage compounds

KW - carbocations

KW - electrocyclic reactions

KW - homogeneous catalysis

KW - supramolecular chemistry

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Enzyme-like control of carbocation deprotonation regioselectivity in supramolecular catalysis of the nazarov cyclization

Abstract

Keywords

ASJC Scopus subject areas

Online availability

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