Unusual route of hydrogenation of diethyl (4R)-[(4-hydroxy-4,5-dihydrofuran-2-yl)methyl]-phosphonate
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It has previously been shown that diethyl (4R)-(4,5-dihydroxypenta-1,2-dienyl)phosphonate (1) undergoes an intramolecular cyclization involving the central carbon atom of the cumulene system and the terminal hydroxyl group under basic catalytic conditions to form diethyl (4R)-[(4-hydroxy-4,5-dihydrofuran-2-yl)methyl]phosphonate (2) . Phosphonate 2 is a highly reactive compound and is of interest as a structural unit for creating biologically active phosphonates.
Keywordsdihydrofuran phosphoorganic compounds hydrogenation tautomerism
- 1.V. K. Brel, Synthesis, 1539 (2001).Google Scholar