Issue 13, 1992

Olivanic acid analogues. Part 11. Ozonolysis of α-ethylideneazetidinones: ozonide fragmentation to α-amino acid-N-carboxyanhydrides

Abstract

Ozonolysis of (E)-7-ethylidene[3-oxa-1-azabicyclo[4.2.0]octane-2-spirocyclohexan]-8-one failed to provide the α-oxoazetidinone 2, but afforded an α-amino acid-N-carboxyanhydride [3,8-dioxa-1-azabicyclo[4.3.0]nonane-2-spirocyclohexane]-7,9-dione 5. [3-Oxa-1-azabicyclo[4.2.0]octane-2-spirocyclohexane]-7,8-dione 2 was instead obtained from the trans-ketone 9 by a sequence involving Baeyer–Villiger oxidation of the azido ketone 10.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1992, 1577-1581

Olivanic acid analogues. Part 11. Ozonolysis of α-ethylideneazetidinones: ozonide fragmentation to α-amino acid-N-carboxyanhydrides

J. H. Bateson, S. C. M. Fell, A. C. Kaura and R. Southgate, J. Chem. Soc., Perkin Trans. 1, 1992, 1577 DOI: 10.1039/P19920001577

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