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Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers

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Abstract

A new cascade process has been accomplished for the synthesis of tetrahydro-1H-cyclopenta[c]furans through palladium-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides. Notably, the key feature of this transformation is the use of vinyl bromides as the C1 building block. Various functionalized tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers could be obtained in good yields with excellent diastereoselectivities.

Graphical abstract: Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers

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Publication details

The article was received on 28 Mar 2017, accepted on 04 May 2017 and first published on 05 May 2017


Article type: Paper
DOI: 10.1039/C7OB00768J
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers

    Y. Diao, Z. Zuo, H. Wang, J. Liu and X. Luan, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00768J

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