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Communication

A New Approach to the Nazarov Reaction via Sequential Electrocyclic Ring Opening and Ring Closure

Supporting Info

Tina N. Grant and F. G. West*

Department of Chemistry, University of Alberta, Edmonton, Alta., Canada T6G 2G2

J. Am. Chem. Soc., 2006, 128 (29), pp 9348–9349

DOI: 10.1021/ja063421a

Publication Date (Web): July 4, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, frederick.west@ualberta.ca

Abstract

Regioselective dichlorocyclopropanation of 2-silyloxydienes furnishes vinylcyclopropanol silyl ethers in good yield. Treatment with silver(I) at room temperature effects disrotatory electrocyclic opening to a 2-chloro-3-silyloxypentadienyl cation, which then undergoes conrotatory (Nazarov) electrocyclization to provide chlorocyclopentenones. This two-step sequence offers a convenient and mild alternative to the standard Nazarov cyclization protocol via a formal 4+1 construction and furnishes products containing useful halogen functionality. In one case possessing a pendant phenyl group, interrupted Nazarov reaction to give a benzohydrindenone was observed.

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Published In Issue July 26, 2006
Received May 16, 2006

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Communication

A New Approach to the Nazarov Reaction via Sequential Electrocyclic Ring Opening and Ring Closure

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Cyclization of Cross-Conjugated Trienes: The Vinylogous Nazarov Reaction

Total Synthesis of (−)-Acutumine

Lanthanum(III) Triflate-Catalyzed Cyclopropanation via Intramolecular Methylene Transfer

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