Synthesis of cyclohexanes via [3 + 3] hexannulation of cyclopropanes and 2-chloromethyl allylsilanes.
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.
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada, N6A 5B7.
Katarina
K
Sapeta
Michael A
MA
Kerr
D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D003510:Cyclohexanes; D003521:Cyclopropanes; D012821:Silanes