Tetrahedron letters

Cyclofunctionalisation reactions of epoxyalcohol derivatives. 3. cyclisationacyl migration of n-benzoylcarbamates to stereodefined oxazolidinones. A new, …

SW McCombie, TL Nagabhushan

Index: McCombie, S. W.; Nagabhushan, T. L. Tetrahedron Letters, 1987 , vol. 28, # 45 p. 5395 - 5398

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Citation Number: 39

Abstract

Abstract: N-Benzoylcarbamates formed in situ from 2, 3-epoxyalcohols and PhCONCO undergo clean N to C-2 cyclisation--followed by N to 0 acy/migration on treatment with catalytic sodium imidazolide or other bases Subsequent benzoate cleavage (NaOMe) is accompanied by equilibration of the N-unsubstituted oxazolidinones; cleavage applied in a for intramolecular delivery of carbon'and oxygen'to C-2 of epoxyalcohol derivatives under ...