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Diastereoselective bicyclization of enynols via gold catalysis

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Abstract

A Au(I)-catalyzed protocol for the cycloisomerizations of enynols into 4.3.0 (hetero)bicycles with complete regio- and diastereoselection is herein described. The sequential bicyclization exploits substrates with a styryl arm, disclosing in turn a reactive pathway that is complementary to the literature reports. The use of a gold(I)–phosphite catalyst allowed for the synthesis of functionalized polycycles under mild conditions, with good yields and low catalyst loadings (1 mol%).

Graphical abstract: Diastereoselective bicyclization of enynols via gold catalysis

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Publication details

The article was received on 31 Jul 2019, accepted on 05 Sep 2019 and first published on 06 Sep 2019


Article type: Research Article
DOI: 10.1039/C9QO00963A
Org. Chem. Front., 2019, Advance Article

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    Diastereoselective bicyclization of enynols via gold catalysis

    C. Cecchini, G. Cera, M. Lanzi, L. Marchiò, M. Malacria and G. Maestri, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00963A

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