Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans

Jingqi Wang; Erika A. Crane; Karl A. Scheidt

doi:10.1021/ol200987c

Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans

Jingqi Wang, Erika A. Crane, Karl A. Scheidt

Chemistry

Research output: Contribution to journal › Article › peer-review

70 Scopus citations

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 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.

Original language	English (US)
Pages (from-to)	3086-3089
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	12
DOIs	https://doi.org/10.1021/ol200987c
State	Published - Jun 17 2011

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200987c

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title = "Highly stereoselective Br{\o}nsted acid catalyzed synthesis of spirooxindole pyrans",

abstract = "A Br{\o}nsted 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.",

author = "Jingqi Wang and Crane, {Erika A.} and Scheidt, {Karl A.}",

year = "2011",

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AU - Wang, Jingqi

AU - Crane, Erika A.

AU - Scheidt, Karl A.

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Y1 - 2011/6/17

N2 - 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.

AB - 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.

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Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans

Abstract

ASJC Scopus subject areas

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CCDC 803480: Experimental Crystal Structure Determination

CCDC 803846: Experimental Crystal Structure Determination

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Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 803480: Experimental Crystal Structure Determination

CCDC 803846: Experimental Crystal Structure Determination

Cite this