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Conversion of 3-cyclopentenyl hydroperoxide into 5-substituted-2,3-dioxabicyclo[2.2.1]heptanes

✍ Scribed by A.J. Bloodworth; H.J. Eggelte

Book ID: 108382256
Publisher: Elsevier Science
Year: 1980
Tongue: French
Weight: 180 KB
Volume: 21
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)93668-2

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The l-azabicyclo[2.2. I]heptan-3-exo-ol (2) was resolved by fractional crystallisation of its hydrogen tartrate salts. The enantiomers (+)-and (-)-2 were oxidised to the ketones (-)-4 and (+)-4, respectively (Scheme). CD spectroscopy suggested that (-)-4 possesses the (IR,4S)-configuration. This abs