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Communication | Special issue | Vol 80, No. 2, 2010, pp.805-810
Published online, 9th September, 2009
DOI: 10.3987/COM-09-S(S)87
Methyl Insertion Reactions of Tetrahydropyrans Having a C1’-Mesyloxy Group on the C2-Side Chain with Trimethylaluminum

Keigo Nakamura, Atsushi Kimishima, and Tadashi Nakata*

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

Abstract

Methyl insertion reactions of tetrahydropyrans having a C1’-mesyloxy group on the C2-side chain, mediated by trimethylaluminum, were investigated. Removal of the mesyloxy group, 1,2-hydride shift and/or ring-expansion, and methyl insertion took place concertedly, depending on the stereostructure of the substrate, to give 2-methylated tetrahydropyran and/or 2- or 3-methylated oxepane.