Intramolecular Hydrogen Bonding (P O--H) Stabilizes the Chair Conformation of Six-Membered Ring Phosphates

S Cruz-Gregorio, M Sanchez…

Index: Cruz-Gregorio, Silvano; Sanchez, Mario; Clara-Sosa, Angel; Bernes, Sylvain; Quintero, Leticia; Sartillo-Piscil, Fernando Journal of Organic Chemistry, 2005 , vol. 70, # 18 p. 7107 - 7113

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Citation Number: 19

Abstract

Six-membered cyclic phosphates (2-phenoxy-2-oxo-1, 3, 2-dioxaphosphorinanes) bearing an internal protected or unprotected hydroxyl group were designed, synthesized, and studied by NMR and computational methods. Selective opening of O-isopropylidene- protected 1, 2-diols at the primary site was achieved with either triethylsilane or trimethylallylsilane in the presence of BF3⊙ OEt2. Applied to 5, 6-O- ...