Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones

Mamatha Amireddy; Kwunmin Chen

doi:10.1016/j.tet.2015.08.061

Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones

Mamatha Amireddy
, Kwunmin Chen^*

^*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

26 引文斯高帕斯（Scopus）

摘要

The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20:1 dr and 86% ee).

原文	英語
頁（從 - 到）	8003-8008
頁數	6
期刊	Tetrahedron
卷	71
發行號	42
DOIs	https://doi.org/10.1016/j.tet.2015.08.061
出版狀態	已發佈 - 2015 10月 21

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tet.2015.08.061

其它文件與鏈接

CCDC 1056328: Experimental Crystal Structure Determination
Amireddy, M. (Creator) & Chen, K. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc14g63x, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc14g63x&sid=DataCite
資料集: Dataset

引用此

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title = "Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones",

abstract = "The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97\%; up to >20:1 dr and 86\% ee).",

keywords = "2-Arylideneindane-1 3-diones, Cascade reaction, Michael-aldol, Squaramide-catalyst, γ-Nitro ketones",

author = "Mamatha Amireddy and Kwunmin Chen",

year = "2015",

month = oct,

day = "21",

doi = "10.1016/j.tet.2015.08.061",

language = "English",

volume = "71",

pages = "8003--8008",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

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T1 - Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones

AU - Amireddy, Mamatha

AU - Chen, Kwunmin

PY - 2015/10/21

Y1 - 2015/10/21

N2 - The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20:1 dr and 86% ee).

AB - The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20:1 dr and 86% ee).

KW - 2-Arylideneindane-1 3-diones

KW - Cascade reaction

KW - Michael-aldol

KW - Squaramide-catalyst

KW - γ-Nitro ketones

UR - https://www.scopus.com/pages/publications/84952874802

UR - https://www.scopus.com/pages/publications/84952874802#tab=citedBy

U2 - 10.1016/j.tet.2015.08.061

DO - 10.1016/j.tet.2015.08.061

M3 - Article

AN - SCOPUS:84952874802

SN - 0040-4020

VL - 71

SP - 8003

EP - 8008

JO - Tetrahedron

JF - Tetrahedron

IS - 42

ER -

Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1056328: Experimental Crystal Structure Determination

引用此