Stereochemical differentiation in the reactions of organometallic reagents with levoglucosenone and some of its dihydro derivatives |
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| Authors: | I. P. Tsypysheva F. A. Valeev E. V. Vasil'eva L. V. Spirikhin G. A. Tolstikov |
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| Affiliation: | (1) Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054 Ufa, Russian Federation |
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| Abstract: | The reactions of methylmanganese iodide with levoglucosenone, its dihydro derivative, and 1.6-anhydro-3-deoxy-4-O-methyl-β-d-erythro-hexopyran-2-ulose were found to be highly diastereoselective compared to the reactions of Li-, Mg-, and Cu-based reagents. This specific feature of the manganese reagent is due to the enhanced tendency of manganese for chelation. Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1240–1243, July, 2000. |
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| Keywords: | levoglucosenone chelate control organometallic reagent diastereoselectivity |
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