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Synthesis of trans-Cycloalkenes via Enantioselective Cyclopropanation and Skeletal Rearrangement

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posted on 2014-11-12, 00:00 authored by Tomoya Miura, Takayuki Nakamuro, Chia-Jung Liang, Masahiro Murakami
An efficient one-pot two-step procedure for asymmetric synthesis of piperidine-fused trans-cycloalkenes is reported. The method comprises the initial enantioselective installation of another cyclopropane ring onto methylene­cyclo­pro­panes and the subsequent thermal skeletal rearrangement in which the installed and inherent cyclopropane rings are both opened. A concerted mechanism is proposed for the latter thermal rearrangement reaction together with a closed transition state model.