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Highly stereoselective Bronsted acid catalyzed synthesis of spirooxindole pyrans.

ABSTRACT: A Brønsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a ?-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.

SUBMITTER: Wang J

PROVIDER: S-EPMC3115630 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans.

Wang Jingqi J Crane Erika A EA Scheidt Karl A KA

Organic letters 20110518 12

A Brønsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a β-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones. ...[more]

PMID: 21591768

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