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Synthesis 2014; 46(15): 2085-2092
DOI: 10.1055/s-0033-1341157
DOI: 10.1055/s-0033-1341157
paper
Ethoxide-Mediated Condensation of γ-tert-Butylallenoate and Aldehydes: Facile Stereoselective Synthesis of Conjugated Dienes and Enynes
Further Information
Publication History
Received: 12 March 2014
Accepted after revision: 18 March 2014
Publication Date:
10 April 2014 (online)
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Abstract
The condensation reaction of a γ-tert-butylallenoate, ethyl 5,5-dimethylhexa-2,3-dienoate, and aldehydes in the presence of sodium ethoxide is described. A range of aldehydes readily reacts with γ-tert-butylallenoate and ethoxide providing a straightforward synthesis of 1,2,3,4-tetrasubstituted conjugated dienes in moderate to good yields and exclusive E,E selectivity. For some aldehydes, the condensation chemoselectively delivers conjugated enynes in good yields and exclusive E selectivity.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
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For recent selected examples for diene synthesis, see:
For selected reviews, see:
For selected examples, see:
Analogous synthesis of enynes from allenoates and aldehydes was reported, see: