Coupling Reactions of Anhydro-Aldose Tosylhydrazones with Boronic Acids |
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| Authors: | Tímea Kaszs Balzs ron Barth Bernadett Balzs Tekla Blga Lszl Juhsz Lszl Somsk Marietta Tth |
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| Institution: | Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary; (T.K.); (B.Á.B.); (B.B.); (T.B.); (L.J.) |
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| Abstract: | A catalyst-free coupling reaction between O-peracetylated, O-perbenzoylated, O-permethylated, and O-permethoxymethylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) and aromatic boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope. The main products in most of the transformations were open-chain 1-C-aryl-hept-1-enitol type compounds while the expected β-d-glycopyranosylmethyl arenes (benzyl C-glycosides) were formed in subordinate yields only. A mechanistic rationale is provided to explain how a complex substrate may change the well-established course of the reaction. |
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| Keywords: | coupling anhydro-aldose tosylhydrazones C-glycosides heptenitols |
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