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^*

^*Corresponding author for this work

Department of Chemistry

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

24 Citations (Scopus)

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).

Original language	English
Pages (from-to)	8003-8008
Number of pages	6
Journal	Tetrahedron
Volume	71
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2015.08.061
Publication status	Published - 2015 Oct 21

Keywords

2-Arylideneindane-1 3-diones
Cascade reaction
Michael-aldol
Squaramide-catalyst
γ-Nitro ketones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2015.08.061

Cite this

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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",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "42",

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TY - JOUR

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

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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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1056328: Experimental Crystal Structure Determination

Cite this

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

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1056328: Experimental Crystal Structure Determination

Cite this