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Synthesis 2014; 46(17): 2353-2361
DOI: 10.1055/s-0034-1378231
DOI: 10.1055/s-0034-1378231
paper
One-Pot Multistep Synthesis of Trisubstituted Alkenes from N-Tosylhydrazones and Alcohols
Further Information
Publication History
Received: 17 March 2014
Accepted after revision: 06 May 2014
Publication Date:
10 June 2014 (online)
Abstract
A one-pot procedure for the synthesis of trisubstituted alkenes from N-tosylhydrazones and alcohols is reported. This procedure combines the aerobic oxidation reaction and Wittig reaction in one pot, which avoids using of environmentally toxic oxidants and isolation of the intermediates. The simple procedure makes it very attractive for the synthesis of trisubstituted alkenes when alcohols are used as starting materials. A variety of trisubstituted alkenes as well as trifluoromethyl-substituted alkenes were obtained in moderate to good yields (up to 84%) with good E-selectivity (up to 99%).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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For selected reviews on the synthesis of trisubstituted alkenes, see:
Mo-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
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