Organocatalytic Asymmetric Michael Addition of Anthrone with β-Nitroolefins

doi:10.11944/j.issn.1000-0518.2015.04.140313

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (4): 422-427.DOI: 10.11944/j.issn.1000-0518.2015.04.140313

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Organocatalytic Asymmetric Michael Addition of Anthrone with β-Nitroolefins

ZHANG Tianyi, NIAN Wenxia, JIN Ying^*

Department of Pharmaceutical Chemistry,Jilin Medical College,Jilin,Jilin 132013,China

Received:2014-09-09 Revised:2015-03-02 Published:2015-04-10 Online:2015-04-10
Contact: Corresponding author:JIN Ying, professor; Tel:0432-64560532; Fax:0432-64560316; E-mail:jinying1021@sina.com; Research interests:asymmetric catalysis and organic synthesis
Supported by:
Supported by the National Natural Science Foundation of China(No.21102055), the Natural Science Foundation of Jilin Province of China(No.201015237)

Abstract

Abstract:

Cinchona alkaloid derivatives as organocatalysts were applied in asymmetric Michael addition reaction of anthrone with various trans-β-nitroolefins. Solvent, temperature and catalyst loading were screened. The optimized conditions are using toluene as the solvent with a 5%(molar fraction) loading of catalyst 1b at room temperature. The products are obtained in 91%~99% yield with up to 95%ee.

Key words: Cinchona alkaloid derivative, organocatalysis, asymmetric Michael addition, anthrone, β-nitroolefins

CLC Number:

O621.3

ZHANG Tianyi, NIAN Wenxia, JIN Ying . Organocatalytic Asymmetric Michael Addition of Anthrone with β-Nitroolefins[J]. Chinese Journal of Applied Chemistry, 2015, 32(4): 422-427.

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Organocatalytic Asymmetric Michael Addition of Anthrone with β-Nitroolefins

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