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Gold-Catalyzed Synthesis of Bicyclo[4.3.0]nonadiene Derivatives via Tandem 6-<i>endo-dig</i>/Nazarov Cyclization of 1,6-Allenynes

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Catalytic cyclization of 1,6-allenynes was achieved by AuPPh3SbF6 (5 mol %) in cold CH2Cl2 (0 °C, 0.5−4 h) to form bicyclo[4.3.0]nonadiene products; this cyclization proceeded more efficiently for a substrate bearing R = alkyl (yields >70%). We propose a reaction mechanism involving a 6-endo-dig cyclization of Au(I)-π-alkyne, followed by Nazarov cyclization.

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2016-06-03
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