Tetrahedron letters

Diastereoselective preparation of novel tetrahydrooxazinones via heterocycloaddition of N-Boc, O-Me-acetals

P Gizecki, RA Youcef, C Poulard, R Dhal, G Dujardin

Index: Gizecki, Patricia; Ait Youcef, Ramzi; Poulard, Celine; Dhal, Robert; Dujardin, Gilles Tetrahedron Letters, 2004 , vol. 45, # 52 p. 9589 - 9592

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Citation Number: 23

Abstract

Under Lewis acid conditions, reaction of N-Boc, O-Me acetals with the (R)-(+)-O-vinyl- pantolactone does not lead to the expected dihydrooxazine, but to the corresponding tetrahydrooxazinone, as a result of the loss of the t-Bu group. A diastereoselective and asymmetrical way to these new heterocyclic compounds is described, together with the first evidence of their ability to undergo N-acylation.