A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

Shu Mei Yang; Praneeth Karanam; Min Wang; Yeong Jiunn Jang; Yu Sheng Yeh; Ping Yao Tseng; Madhusudhan Reddy Ganapuram; Yan Cheng Liou; Wenwei Lin

doi:10.1039/c8cc09219b

A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

Shu Mei Yang, Praneeth Karanam, Min Wang, Yeong Jiunn Jang, Yu Sheng Yeh, Ping Yao Tseng, Madhusudhan Reddy Ganapuram, Yan Cheng Liou, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

32 Citations (Scopus)

Abstract

An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene oxindoles to fully substituted enones and demonstrates the usefulness of the latter as efficient Michael acceptors in generating complex caged products in 26-92% yields, 14-98% ee and up to >25:1 d.r. values.

Original language	English
Pages (from-to)	1398-1401
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	10
DOIs	https://doi.org/10.1039/c8cc09219b
Publication status	Published - 2019

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c8cc09219b

Cite this

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title = "A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters",

abstract = "An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene oxindoles to fully substituted enones and demonstrates the usefulness of the latter as efficient Michael acceptors in generating complex caged products in 26-92% yields, 14-98% ee and up to >25:1 d.r. values.",

author = "Yang, {Shu Mei} and Praneeth Karanam and Min Wang and Jang, {Yeong Jiunn} and Yeh, {Yu Sheng} and Tseng, {Ping Yao} and Ganapuram, {Madhusudhan Reddy} and Liou, {Yan Cheng} and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/c8cc09219b",

language = "English",

volume = "55",

pages = "1398--1401",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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T1 - A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

AU - Yang, Shu Mei

AU - Karanam, Praneeth

AU - Wang, Min

AU - Jang, Yeong Jiunn

AU - Yeh, Yu Sheng

AU - Tseng, Ping Yao

AU - Ganapuram, Madhusudhan Reddy

AU - Liou, Yan Cheng

AU - Lin, Wenwei

PY - 2019

Y1 - 2019

N2 - An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene oxindoles to fully substituted enones and demonstrates the usefulness of the latter as efficient Michael acceptors in generating complex caged products in 26-92% yields, 14-98% ee and up to >25:1 d.r. values.

AB - An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene oxindoles to fully substituted enones and demonstrates the usefulness of the latter as efficient Michael acceptors in generating complex caged products in 26-92% yields, 14-98% ee and up to >25:1 d.r. values.

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JO - Chemical Communications

JF - Chemical Communications

IS - 10

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A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

Abstract

ASJC Scopus subject areas

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CCDC 1528078: Experimental Crystal Structure Determination

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A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1528078: Experimental Crystal Structure Determination

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