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Synfacts 2011(3): 0288-0288
DOI: 10.1055/s-0030-1259490
DOI: 10.1055/s-0030-1259490
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium-Catalyzed Asymmetric Synthesis of Allenylsilanes
M. Ogasawara*, A. Okada, V. Subbarayan, S. Sörgel, T. Takahashi*
Hokkaido University, Sapporo, Japan
Further Information
Publication History
Publication Date:
16 February 2011 (online)
Significance
Bromosilyldienes undergo reaction with malonate-derived nucleophiles in the presence of a palladium and a chiral phosphine ligand to generate chiral allenylsilanes in high %ee. The products can react with various electrophiles, generating tertiary and quaternary propargyl carbons with nearly complete axial chirality transfer.