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Synthesis 2013; 45(9): 1261-1269
DOI: 10.1055/s-0032-1316884
DOI: 10.1055/s-0032-1316884
paper
Palladium-Catalyzed Intramolecular Oxidative Heck Cyclization and Its Application toward a Synthesis of (±)-β-Cuparenone Derivatives Supported by Computational Studies
Further Information
Publication History
Received: 16 November 2012
Accepted after revision: 11 March 2013
Publication Date:
08 April 2013 (online)
Abstract
A novel and efficient intramolecular oxidative cyclization of substituted homoallylic alcohols to form cyclic keto compounds under palladium-catalyzed conditions is described. The reaction has practical applications in the synthesis of sesquiterpenes. The mechanism of cyclization, the key step in the tandem reaction, was analyzed by using density functional theory calculations.
Key words
palladium - Heck reaction - cyclizations - terpenoids - ketones - alkenes - catalysis - oxidations - computational studiesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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