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Stereoselective Synthesis of 1,2,3,4-Tetrasubstituted Dienes from Allenoates and Aldehydes: An Observation of Phosphine-Induced Chemoselectivity

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posted on 06.08.2010, 00:00 by Silong Xu, Wen Zou, Guiping Wu, Haibin Song, Zhengjie He
Phosphine-mediated olefination between α-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo- and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.