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Synfacts 2006(7): 0707-0707  
DOI: 10.1055/s-2006-941817
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Hydrovinylation of α-Alkyl Vinylarenes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
W.-J. Shi, Q. Zhang, J.-H. Xie, S.-F. Zhu, G.-H. Hou, Q.-L. Zhou*
Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

The authors have developed chiral spiro monophosphorous ligands that are very effective for the hydrovinylation of α-alkyl vinylarenes. The use of ethylene as the vinyl source under nickel catalysis provides the chiral products with very high chemo- and enantioselectivity. Various substitution on the aryl group is tolerated, including electron-donating (methyl, methoxy) and electron-withdrawing groups (Cl). The size of the R group was shown to directly effect the selectivity, with isopropyl and cyclohexyl groups giving 99% ee.