Synthesis 2014; 46(15): 2085-2092
DOI: 10.1055/s-0033-1341157
paper
© Georg Thieme Verlag Stuttgart · New York

Ethoxide-Mediated Condensation of γ-tert-Butylallenoate and Aldehydes: Facile Stereoselective Synthesis of Conjugated Dienes and Enynes

Silong Xu
a   Department of Chemistry, School of Science, Xi’an Jiaotong University, Xi’an 710049, P. R. of China
,
Liyi Wang
b   The State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), and Department of Chemistry, Nankai University, Tianjin 300071, P. R. of China   Fax: +86(22)23501520   eMail: zhengjiehe@nankai.edu.cn
,
Yuhai Tang
a   Department of Chemistry, School of Science, Xi’an Jiaotong University, Xi’an 710049, P. R. of China
,
Zhengjie He*
b   The State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), and Department of Chemistry, Nankai University, Tianjin 300071, P. R. of China   Fax: +86(22)23501520   eMail: zhengjiehe@nankai.edu.cn
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Publikationsverlauf

Received: 12. März 2014

Accepted after revision: 18. März 2014

Publikationsdatum:
10. April 2014 (online)


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

 
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