New routes to isomerically pure cyclopentanes. Synthesis of (3S, 4S)-3, 4-bis (benzoyloxymethyl) cyclopentan-1-ol using palladium-catalyzed [2+ 3] cycloaddition

M Janson, I Kvarnström, SCT Svensson, B Classon…

Index: Janson; Kvarnstrom; Svensson; Classon; Samuelsson Synthesis, 1993 , # 1 p. 129 - 133

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Citation Number: 7

Abstract

In contrast to our results Trost et al. reported only one single cycloadduct, the enantiomer of 9 a, when using the methyl ester and C-4 epimeric analogue of 7 a in the cycloaddition. This cycloadduct, the enantiomer of 9a having an optical rotation of—9.83 “, was reported to be quantitatively converted to the (E)-enantiomer of 9b, with an optical rotation of—29.04". 28 Degradation of the dioxolane ring in 9 (cis/trans mixture vide supra) was performed by ...