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Communication | Special issue | Vol 66, No. 1, 2005, pp.111-117
Published online, 11th November, 2005
DOI: 10.3987/COM-05-S(K)45
Cu(II)-mediated Stereoselective Michael Addition of a Methyl Group to an α,β-Unsaturated Ester as the C2-Side Chain in 3-(t-Butyldimethylsilyloxy)tetrahydropyrans

Keisuke Suzuki, Ulrike Jannsen, Hiroko Matsukura, and Tadashi Nakata*

*Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

Stereoselective Michael addition of a methyl group to an α,β-unsaturated ester as the C2-side chain in 3-(t-butyldimethylsilyloxy)tetrahydropyrans was accomplished under the conditions using MeMgBr and TMSCl in the presence of a catalytic amount of Cu(N-i-Pr-Sal)2.