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Gold-catalyzed synthesis of bicyclo[4.3.0]nonadiene derivatives via tandem 6-endo-dig/Nazarov cyclization of 1,6-allenynes
Journal article   Peer reviewed

Gold-catalyzed synthesis of bicyclo[4.3.0]nonadiene derivatives via tandem 6-endo-dig/Nazarov cyclization of 1,6-allenynes

Guan-You Lin, Chun-Yao Yang and Rai-Shung Liu
Journal of Organic Chemistry, Vol.72(18), pp.6753-6757
31/08/2007

Abstract

(Chemical Equation Presented) Catalytic cyclization of 1,6-allenynes was achieved by AuPPh <sub>3</sub> SbF <sub>6</sub> (5 mol %) in cold CH <sub>2</sub> Cl <sub>2</sub> (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. © 2007 American Chemical Society.

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