Highly Stereoselective Ring-Opening Addition of Terminal Acetylenes to Bicyclic Olefins Catalyzed by Nickel Complexes

Highly Stereoselective Ring-Opening Addition of Terminal Acetylenes to Bicyclic Olefins Catalyzed by Nickel Complexes

Treatment of 7-oxa- and 7-azabenzonorbornadienes with terminal acetylenes in the presence of Ni(dppe)Cl2, ZnCl2, and Zn powder in toluene at 90 °C afforded the corresponding cis-2-alkynyl-1,2-dihydronaphthalene derivatives in moderate to excellent yields with remarkably high stereoselectivity.

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Veröffentlicht in:Organic letters 2002-05, Vol.4 (10), p.1679-1682
Hauptverfasser: Rayabarapu, Dinesh Kumar, Chiou, Chii-Feng, Cheng, Chien-Hong
Format: Artikel
Sprache:eng
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Zusammenfassung:Treatment of 7-oxa- and 7-azabenzonorbornadienes with terminal acetylenes in the presence of Ni(dppe)Cl2, ZnCl2, and Zn powder in toluene at 90 °C afforded the corresponding cis-2-alkynyl-1,2-dihydronaphthalene derivatives in moderate to excellent yields with remarkably high stereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol025731d