Facile synthesis of highly functionalized six-membered heterocycles via PPh3-catalyzed [4+2] annulations of activated terminal alkynes and hetero-dienes: scope, mechanism, and application

Author: Zhang, Qiongmei; Fang, Tong; Tong, Xiaofeng

Description: A novel [4+2] annulation between activated terminal alkynes and aza-dienes or oxo-dienes has been developed with the use of triphenylphosphine catalyst (20mol%), which provides a facile method for synthesis of the corresponding highly functionalized dihydropyridines or dihydropyrans in good to excellent yields. The reaction mechanism has also been established, consisting of formal hetero-Diels-Alder reaction catalyzed by PPh3 and [1,3]-proton transfer, which exhibits a large isotopic effect.

Subject headings: PPh Catalysis; Hetero-diene; [4+2] Annulations; Heterocycle; H-Transfer; Diels-Alder

Publication year: 2010

Journal or book title: Tetrahedron

Volume: 66

Issue: 40

Pages: 8095-8100

Find the full text: https://www.sciencedirect.com/science/article/pii/S0040402010010914

Find more like this one (cited by): https://scholar.google.com/scholar?cites=11499145606745427655&as_sdt=5,26&sciodt=0,26&hl=en

Serial number: 3344

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