Nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and heteroatom-substituted alkynes: application to selective three-component reaction with 1,3-diynes

Ryu Yamasaki; Natsuki Terashima; Ikuo Sotome; Shunsuke Komagawa; Shinichi Saito

doi:10.1021/jo902251m

Nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and heteroatom-substituted alkynes: application to selective three-component reaction with 1,3-diynes

J Org Chem. 2010 Jan 15;75(2):480-3. doi: 10.1021/jo902251m.

Authors

Ryu Yamasaki¹, Natsuki Terashima, Ikuo Sotome, Shunsuke Komagawa, Shinichi Saito

Affiliation

¹ Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo, Japan 162-8601.

PMID: 20014802
DOI: 10.1021/jo902251m

Abstract

Heteroatom-substituted alkynes such as ynol ethers and ynamines turned out to be decent substrates for the Ni-catalyzed [3 + 2 + 2] cocyclization of ethyl cyclopropylideneacetate (1). The three-component cocyclization of 1, 1,3-diynes, and heteroatom-substituted alkynes also proceeded selectively. The study provided an efficient method for the synthesis of heteroatom-substituted cycloheptadiene and related compounds.