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

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 w...

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Main Authors:	Ana M. Sanjuán, Alberto Martínez, Patricia García-García, Manuel A. Fernández-Rodríguez, Roberto Sanz
Format:	Article
Language:	English
Published:	Beilstein-Institut 2013-10-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	catalysis dihydronaphthalenes gold gold catalysis hydroxycyclization selectivity
Online Access:	https://doi.org/10.3762/bjoc.9.263

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spelling	doaj-903b05ebdcfc41b3b79d41b748b5c7eb2021-02-02T04:44:50ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-10-01912242224910.3762/bjoc.9.2631860-5397-9-263Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynesAna M. Sanjuán0Alberto Martínez1Patricia García-García2Manuel A. Fernández-Rodríguez3Roberto Sanz4Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainÁrea de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainÁrea de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainÁrea de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainÁrea de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainThe 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.https://doi.org/10.3762/bjoc.9.263catalysisdihydronaphthalenesgoldgold catalysishydroxycyclizationselectivity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Ana M. Sanjuán Alberto Martínez Patricia García-García Manuel A. Fernández-Rodríguez Roberto Sanz
spellingShingle	Ana M. Sanjuán Alberto Martínez Patricia García-García Manuel A. Fernández-Rodríguez Roberto Sanz Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes Beilstein Journal of Organic Chemistry catalysis dihydronaphthalenes gold gold catalysis hydroxycyclization selectivity
author_facet	Ana M. Sanjuán Alberto Martínez Patricia García-García Manuel A. Fernández-Rodríguez Roberto Sanz
author_sort	Ana M. Sanjuán
title	Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes
title_short	Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes
title_full	Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes
title_fullStr	Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes
title_full_unstemmed	Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes
title_sort	gold(i)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2013-10-01
description	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.
topic	catalysis dihydronaphthalenes gold gold catalysis hydroxycyclization selectivity
url	https://doi.org/10.3762/bjoc.9.263
work_keys_str_mv	AT anamsanjuan goldicatalyzed6endohydroxycyclizationof7substituted16enynes AT albertomartinez goldicatalyzed6endohydroxycyclizationof7substituted16enynes AT patriciagarciagarcia goldicatalyzed6endohydroxycyclizationof7substituted16enynes AT manuelafernandezrodriguez goldicatalyzed6endohydroxycyclizationof7substituted16enynes AT robertosanz goldicatalyzed6endohydroxycyclizationof7substituted16enynes
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Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes

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