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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2007-08, Vol.72 (18), p.6753-6757
Hauptverfasser: Lin, Guan-You, Yang, Chun-Yao, Liu, Rai-Shung
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0707939