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Gold-catalyzed intramolecular allylation of silyl alkynes induced by silane alcoholysis.

ABSTRACT: The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.

SUBMITTER: Park S 

PROVIDER: S-EPMC2569199 | biostudies-literature | 2006 Aug

REPOSITORIES: biostudies-literature

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Gold-catalyzed intramolecular allylation of silyl alkynes induced by silane alcoholysis.

Park Sangho S   Lee Daesung D  

Journal of the American Chemical Society 20060801 33

The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross meta  ...[more]