Tetrahedron letters

Reaction of small-size cycloalkane rings with RuO 4. Oxidative scission of ethyl 2, 2-dimethoxycyclopropane-1-carboxylates and methyl 2, 2, 6, 6-tetramethoxybicyclo [ …

ML Graziano, M Lasalvia, V Piccialli, D Sica

Index: Graziano, M. Liliana; Lasalvia, Maria; Piccialli, Vincenzo; Sica, Donato Tetrahedron Letters, 1996 , vol. 37, # 4 p. 527 - 530

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Citation Number: 13

Abstract

The reaction of ethyl 2, 2-dimethoxycyclopropane-1-carboxylates 1a-d and methyl 2, 2, 6, 6- tetramethoxybicyclo [2.2. 0] hexane-1-carboxylates 5a and 5b with RuO4 in CCl4 at room temperature leads in both cases to the oxidative ring opening by regioselective scission of the electron-rich C1 C2 bond for 1a-d, and both C1 C2 and C1 C6 bonds for 5a and 5b. Methyl ethyl oxobutanedioates 2a-d were obtained in the first case while the 3-substituted ...