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Highly anti-Selective Asymmetric Nitro-Mannich Reactions Catalyzed by Bifunctional Amine-Thiourea-Bearing Multiple Hydrogen-Bonding Donors

Chun-Jiang Wang*, Xiu-Qin Dong, Zhi-Hai Zhang, Zhi-Yong Xue and Huai-Long Teng

*College of Chemistry and Molecular Sciences, Wuhan University, P.R. China 430072, Email: cjwangwhu.edu.cn

C.-J. Wang, X.-Q. Dong, Z.-H. Zhang, Z.-Y. Xue, H.-L. Teng, J. Am. Chem. Soc., 2008, 130, 8606-8607.

DOI: 10.1021/ja803538x (free Supporting Information)



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Abstract

A chiral bifunctional multiple hydrogen-bonding-donor amine-thiourea catalyzes a highly anti-selective and enantioselective nitro-Mannich reaction for a broad spectrum of substrates. Multiple hydrogen-bonding donors play a significant role in accelerating reactions and improving yields, diastereoselectivities, and enantioselectivities.

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Key Words

Aza-Henry Reaction, Organocatalysis, Nitro Compounds


ID: J48-Y2008-1950