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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

36 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	1398-1401
頁數	4
期刊	Chemical Communications
卷	55
發行號	10
DOIs	https://doi.org/10.1039/c8cc09219b
出版狀態	已發佈 - 2019

ASJC Scopus subject areas

催化
電子、光磁材料
陶瓷和複合材料
一般化學
表面、塗料和薄膜
金屬和合金
材料化學

存取文件

10.1039/c8cc09219b

其它文件與鏈接

CCDC 1528078: Experimental Crystal Structure Determination
Yang, S.-M. (Creator), Karanam, P. (Creator), Wang, M. (Creator), Jang, Y.-J. (Creator), Yeh, Y.-S. (Creator), Tseng, P.-Y. (Creator), Ganapuram, M. R. (Creator), Liou, Y.-C. (Creator) & Lin, W. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1n92vw, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n92vw&sid=DataCite
資料集: Dataset

引用此

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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.

UR - https://www.scopus.com/pages/publications/85060619841

UR - https://www.scopus.com/pages/publications/85060619841#tab=citedBy

U2 - 10.1039/c8cc09219b

DO - 10.1039/c8cc09219b

M3 - Article

C2 - 30640327

AN - SCOPUS:85060619841

SN - 1359-7345

VL - 55

SP - 1398

EP - 1401

JO - Chemical Communications

JF - Chemical Communications

IS - 10

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1528078: Experimental Crystal Structure Determination

引用此