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Gold-Catalyzed Vinyl Ether Hydroalkynylation: An Alternative Pathway for the Gold-Catalyzed Intermolecular Reaction of Alkenes and Alkynes.

ABSTRACT: In this report, the gold-catalyzed intermolecular reaction of vinyl ethers and terminal alkynes is investigated. Utilizing a triazole gold catalyst lessens gold decomposition in the presence of the vinyl ether and affords an alkynylation product instead of the [2 + 2] product. This protocol has been expanded to include glycal substrates, which undergo a one-pot alkynylation-Ferrier reaction to produce functionalized sugars in moderate to excellent yields with high diastereoselectivity.

SUBMITTER: Hosseyni S

PROVIDER: S-EPMC6430632 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Gold-Catalyzed Vinyl Ether Hydroalkynylation: An Alternative Pathway for the Gold-Catalyzed Intermolecular Reaction of Alkenes and Alkynes.

Hosseyni Seyedmorteza S Smith Courtney A CA Shi Xiaodong X

Organic letters 20161129 24

In this report, the gold-catalyzed intermolecular reaction of vinyl ethers and terminal alkynes is investigated. Utilizing a triazole gold catalyst lessens gold decomposition in the presence of the vinyl ether and affords an alkynylation product instead of the [2 + 2] product. This protocol has been expanded to include glycal substrates, which undergo a one-pot alkynylation-Ferrier reaction to produce functionalized sugars in moderate to excellent yields with high diastereoselectivity. ...[more]

PMID: 27978688

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