Pyrrolidine-linker-camphor assembly: Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions

Shaik Anwar; Pei Hsun Lee; Tsai Yung Chou; Chihliang Chang; Kwunmin Chen

doi:10.1016/j.tet.2010.11.093

Pyrrolidine-linker-camphor assembly: Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions

Shaik Anwar, Pei Hsun Lee, Tsai Yung Chou, Chihliang Chang, Kwunmin Chen

Department of Chemistry

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

17 Citations (Scopus)

Abstract

A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.

Original language	English
Pages (from-to)	1171-1177
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	6
DOIs	https://doi.org/10.1016/j.tet.2010.11.093
Publication status	Published - 2011 Feb 11

Keywords

Camphor
Linker
Michael addition
Nitroolefins
Organocatalysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2010.11.093

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title = "Pyrrolidine-linker-camphor assembly: Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions",

abstract = "A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.",

keywords = "Camphor, Linker, Michael addition, Nitroolefins, Organocatalysis",

author = "Shaik Anwar and Lee, {Pei Hsun} and Chou, {Tsai Yung} and Chihliang Chang and Kwunmin Chen",

note = "Funding Information: We thank the National Science Council of the Republic of China ( NSC 99-2113-M-003-002-MY3 and NSC 99-2119-M-003-001-MY2 ) and National Taiwan Normal University ( 99T3030-5 and 99-D ) for financial support of this work. Our gratitude goes to the Academic Paper Editing Clinic at NTNU, and to the National Center for High-Performance Computing for providing us with computer time and facilities. Copyright: Copyright 2011 Elsevier B.V., All rights reserved.",

year = "2011",

month = feb,

day = "11",

doi = "10.1016/j.tet.2010.11.093",

language = "English",

volume = "67",

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AU - Anwar, Shaik

AU - Lee, Pei Hsun

AU - Chou, Tsai Yung

AU - Chang, Chihliang

AU - Chen, Kwunmin

N1 - Funding Information: We thank the National Science Council of the Republic of China ( NSC 99-2113-M-003-002-MY3 and NSC 99-2119-M-003-001-MY2 ) and National Taiwan Normal University ( 99T3030-5 and 99-D ) for financial support of this work. Our gratitude goes to the Academic Paper Editing Clinic at NTNU, and to the National Center for High-Performance Computing for providing us with computer time and facilities. Copyright: Copyright 2011 Elsevier B.V., All rights reserved.

PY - 2011/2/11

Y1 - 2011/2/11

N2 - A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.

AB - A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.

KW - Camphor

KW - Linker

KW - Michael addition

KW - Nitroolefins

KW - Organocatalysis

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JO - Tetrahedron

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Pyrrolidine-linker-camphor assembly: Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions

Abstract

Keywords

ASJC Scopus subject areas

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