Issue 38, 2009

Interrupting the Nazarov reaction: domino and cascade processes utilizing cyclopentenyl cations

Abstract

The Nazarov reaction entails the electrocyclic closure of a conjugated pentadienyl cation to furnish a cyclopentenyl cation. In its conventional protocol, this intermediate is allowed to undergo elimination through loss of an adjacent proton, providing cyclopentenone products. This feature article describes a relatively new class of domino and cascade processes in which the mechanistic course of the Nazarov reaction is diverted at the point of the cyclopentenyl cation intermediate, collectively referred to as “interrupted Nazarov reactions.” A variety of intra- or intermolecular nucleophiles, including silyl hydrides, alkenes, arenes, amines, halides, oxygen nucleophiles and azides, can capture the cation at one terminus, resulting in interesting polycyclic structures. 1,3-Dienes also trap the cyclopentenyl cation, but in this case via concerted [4 + 3]-cycloaddition to give keto-bridged cyclooctenes. An alternative method for generating the pentadienyl cyclization precursor from dichlorocyclopropanes rather than cross-conjugated dienones is also discussed, along with some novel trapping processes.

Graphical abstract: Interrupting the Nazarov reaction: domino and cascade processes utilizing cyclopentenyl cations

Article information

Article type
Feature Article
Submitted
29 Apr 2009
Accepted
14 Jul 2009
First published
21 Aug 2009

Chem. Commun., 2009, 5676-5688

Interrupting the Nazarov reaction: domino and cascade processes utilizing cyclopentenyl cations

T. N. Grant, C. J. Rieder and F. G. West, Chem. Commun., 2009, 5676 DOI: 10.1039/B908515G

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