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Synfacts 2007(9): 0964-0964  
DOI: 10.1055/s-2007-968861
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Regio- and Stereoselective Allylic Alkylation of Acyclic Ketone Enolates

Contributor(s): Hisashi Yamamoto, Marina Naodovic
W.-H Zheng, B.-H. Zheng, Y. Zhang, X.-L. Hou*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

This is one of the first successful examples of formation of two chiral centers via transition-metal-catalyzed reaction between enolates of simple ketones and monosubstituted allylic substrates. A ferrocene-based ligand in combination with an allylpalladium species smoothly affords homoallyl ketones with high diastereo- and enantio­selectivities. An interesting observation has been made regarding additives and solvents used, which can completely switch the regioselectivity of the reaction.