Synfacts 2011(3): 0288-0288  
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

Contributor(s): Hisashi Yamamoto, Patrick Brady
M. Ogasawara*, A. Okada, V. Subbarayan, S. Sörgel, T. Takahashi*
Hokkaido University, Sapporo, Japan
Further Information

Publication History

Publication Date:
16 February 2011 (online)


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.