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

Author

Silong Xu, Llyl Wang, Yuhal Tang, and Zhengjie He

Subjects
CONDENSATION, BUTYL group, SODIUM compounds, ALDEHYDES, DIOLEFINS, CHEMOSELECTIVITY
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. [ABSTRACT FROM AUTHOR]

Published
2014
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