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Nickel-Catalyzed Highly Regio- and Stereoselective Cyclization of Oxanorbornenes with Alkyl Propiolates: A Novel Method for the Synthesis of Benzocoumarin Derivatives

2001; Wiley; Volume: 40; Issue: 7 Linguagem: Inglês

10.1002/1521-3773(20010401)40

1521-3773

Dinesh Kumar Rayabarapu, Thota Sambaiah, Chien‐Hong Cheng,

Synthesis and Biological Evaluation

7-Oxabenzonorbornadienes bearing various substituents react with propiolates in the presence of [NiBr2(dppe)] (dppe=bis(diphenylphosphanyl)ethane) as a catalyst precursor and zinc powder to give benzocoumarin derivatives [Eq. (1)]. The one-pot reactions proceed at 80°C in acetonitrile, and the products are obtained in good yields with high regio- and stereoselectivity. Supporting information for this article is available on the WWW under http://www.angewandte.com or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.