ChemInform Abstract: Studies on the Regioselectivity of Horner-Wadsworth-Emmons (HWE) Reactions on 3,4-Enuloses. Further Evidence of Phosphonate-Phosphate Rearrangements Through Five-Membered Cyclic Intermediates
In: ChemInform, Jg. 30 (2010-06-12)
Online
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Zugriff:
The Horner-Wadsworth-Emmons (HWE) reaction was performed on methyl 3,6-di-O-benzoyl-2-deoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (1) with the potassium enolates of dimethyl [(methoxycarbonyl)methyl]phosphonate (2) or diethyl [(ethoxycarbonyl) methyl]phosphonate (3) under different conditions (metallic cation and solvent) in order to study regio- and stereochemical aspects of the reaction. In the presence of lithium ions, no reaction took place. When sodium enolates were employed, 1,2-addition was the main reaction in chelating solvents, whereas the 1,4-adduct is favoured in the less polar, non chelating toluene. Only 1,2-addition was observed with potassium enolates. Evidence of phosphonate-phosphate rearrangements through five membered cyclic intermediates is described.
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ChemInform Abstract: Studies on the Regioselectivity of Horner-Wadsworth-Emmons (HWE) Reactions on 3,4-Enuloses. Further Evidence of Phosphonate-Phosphate Rearrangements Through Five-Membered Cyclic Intermediates
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Autor/in / Beteiligte Person: | Alicia Fernández Cirelli ; Moradei, Oscar ; Cecile M. du Mortier |
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Zeitschrift: | ChemInform, Jg. 30 (2010-06-12) |
Veröffentlichung: | Wiley, 2010 |
Medientyp: | unknown |
ISSN: | 1522-2667 (print) ; 0931-7597 (print) |
DOI: | 10.1002/chin.199946193 |
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