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^*

^*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

22 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	1171-1177
頁數	7
期刊	Tetrahedron
卷	67
發行號	6
DOIs	https://doi.org/10.1016/j.tet.2010.11.093
出版狀態	已發佈 - 2011 2月 11

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tet.2010.11.093

其它文件與鏈接

CCDC 796818: Experimental Crystal Structure Determination
Anwar, S. (Creator), Lee, P.-H. (Creator), Chou, T.-Y. (Creator), Chang, C. (Creator) & Chen, K. (Creator), Unknown Publisher, 2011
DOI: 10.5517/ccvr4tj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccvr4tj&sid=DataCite
資料集: Dataset

引用此

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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. ",

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

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T2 - Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions

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.

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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UR - https://www.scopus.com/pages/publications/78751570918#tab=citedBy

U2 - 10.1016/j.tet.2010.11.093

DO - 10.1016/j.tet.2010.11.093

M3 - Article

AN - SCOPUS:78751570918

SN - 0040-4020

VL - 67

SP - 1171

EP - 1177

JO - Tetrahedron

JF - Tetrahedron

IS - 6

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 796818: Experimental Crystal Structure Determination

引用此