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Enantioselective Conjugate Addition of Both Aromatic Ketones and Acetone to Nitroolefins Catalyzed by Chiral Primary Amines Bearing Multiple Hydrogen-Bonding Donors

Zhong-Wen Sun, Fang-Zhi Peng*, Ze-Qian Li, Li-Wei Zou, Shao-Xiong Zhang, Xiang Li and Zhi-Hui Shao*

*Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China, Email: zhihui_shaohotmail.com, pengfangzhiynu.edu.cn

Z.-W. Sun, F.-Z. Peng, Z.-Q. Li, L.-W. Zhou, S.-X. Zhang, X. Li, Z.-H. Shao, J. Org. Chem., 2012, 77, 4103-4110.

DOI: 10.1021/jo300011x



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Abstract

A bifunctional organocatalyst efficiently catalyzed not only enantioselective conjugate addition of aromatic ketones to nitroolefins in good yields with excellent enantioselectivities but also enantioselective conjugate addition of acetone to nitroolefins in excellent yields with high enantioselectivities.

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Key Words

Nitro Compounds, Organocatalysis


ID: J42-Y2012-1190