4.8 Article

Synthesis of Cyclohexanes via [3+3] Hexannulation of Cyclopropanes and 2-Chloromethyl Allylsilanes

Journal

ORGANIC LETTERS
Volume 11, Issue 10, Pages 2081-2084

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900457z

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Lewis acid-assisted ring-opening/allylation of 1,1-cyclopropane diesters, followed by base-mediated ring closure, generates functionalized exo-methylenecyclohexanes in good yield. This two-step procedure is highlighted by expedient preparation of a pyrido[1,2-a]indole skeleton common to the chippiine class of Iboga indole alkaloids.

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