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Communication | Special issue | Vol 86, No. 1, 2012, pp.147-153
Published online, 13th July, 2012
DOI: 10.3987/COM-12-S(N)31
Construction of All-Carbon Quaternary Stereocenters by Zinc-Mediated Barbier-Type Allylation in Aqueous Media

Ken-ichi Takao,* Tomo Miyashita, Nozomi Akiyama, Takuya Kurisu, Kohei Tsunoda, and Kin-ichi Tadano*

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan

Abstract

Stereoselective synthesis of all-carbon quaternary stereocenters by Barbier-type allylation in aqueous media is described. Sugar-derived aldehydes, 2,3-O-isopropylidene-D-glyceraldehyde and 2,4-O-benzylidene-D-threose, were reacted with geranyl chloride in the presence of zinc powder to provide γ-adducts bearing quaternary stereocenters with good stereoselectivity.