Tetrahedron letters

Acid catalysed methanolysis of 2, 5-diazabicyclo [2.2. 2] octane-3, 6-diones: scope and limitations

…, WM De Borggraeve, F Compernolle, GJ Hoornaert

Index: Verbist, Bie M. P.; Smets, Wim J.; De Borggraeve, Wim M.; Compernolle, Frans; Hoornaert, Georges J. Tetrahedron Letters, 2004 , vol. 45, # 22 p. 4371 - 4374

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Citation Number: 5

Abstract

The selective methanolysis of 2, 5-diazabicyclo [2.2. 2] octane-3, 6-dione systems is a key step in a synthetic procedure leading to 4-amino-6-oxo-2-piperidinecarboxylate systems. This reaction seems to be primarily governed by steric hindrance caused by the substituents at the 1-and 4-bridgehead positions of the dione. In absence of bulky substituents the methanolysis is directed by the secondary or tertiary nature of the two lactam moieties.