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Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes.

ABSTRACT: The cyclization of o-(alkynyl)-3-(methylbut-2-enyl)benzenes, 1,6-enynes having a condensed aromatic ring at C3-C4 positions, has been studied under the catalysis of cationic gold(I) complexes. The selective 6-endo-dig mode of cyclization observed for the 7-substituted substrates in the presence of water or methanol giving rise to hydroxy(methoxy)-functionalized dihydronaphthalene derivatives is highly remarkable in the context of the observed reaction pathways for the cycloisomerizations of 1,6-enynes bearing a trisubstituted olefin.

SUBMITTER: Sanjuan AM

PROVIDER: S-EPMC3817472 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes.

Sanjuán Ana M AM Martínez Alberto A García-García Patricia P Fernández-Rodríguez Manuel A MA Sanz Roberto R

Beilstein journal of organic chemistry 20131029

The cyclization of o-(alkynyl)-3-(methylbut-2-enyl)benzenes, 1,6-enynes having a condensed aromatic ring at C3-C4 positions, has been studied under the catalysis of cationic gold(I) complexes. The selective 6-endo-dig mode of cyclization observed for the 7-substituted substrates in the presence of water or methanol giving rise to hydroxy(methoxy)-functionalized dihydronaphthalene derivatives is highly remarkable in the context of the observed reaction pathways for the cycloisomerizations of 1,6- ...[more]

PMID: 24204437

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