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Synfacts 2006(2): 0136-0136  
DOI: 10.1055/s-2005-924773
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral, All-Carbon Quaternary Centers via Allylic Alkylation

Contributor(s): Mark Lautens, Andrew Martins
T. Nemoto, T. Fukuda, T. Matsumoto, T. Hitomi, Y. Hamada*
Chiba University, Japan
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

Asymmetric allylic alkylations have been well explored; however, the enantioselective construction of all-carbon quaternary centers still remains a challenging goal. Using γ-acetoxy-α,β-unsaturated carbonyl compounds as π-allyl precursor and cyclic β-ketoesters as nucleophile in the presence of a Pd catalyst, Zn additive and chiral diaminophosphine oxide ligand (DIAPHOX), a variety of quaternary carbon compounds were synthesized with good to excellent enantioselectivity.