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Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

Jun Jiang, Hua-Dong Xu, Jian-Bei Xi, Bai-Yan Ren, Feng-Ping Lv, Xin Guo, Li-Qin Jiang, Zhi-Yong Zhang and Wen-Hao Hu*

*Department of Chemistry, Institute of Drug Discovery and Development, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China, Email: whuchem.ecnu.edu.cn

J. Jiang, H.-D. Xu, J.-B. Xi, B.-Y. Ren, F.-P. Lv, X. Guo, L.-Q. Jiang, Z.-Y. Zhang, W.-H. Hu, J. Am. Chem. Soc., 2011, 133, 8428-8431.

DOI: 10.1021/ja201589k (free Supporting Information)



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Abstract

The intriguing Rh2(OAc)4 and chiral Brønsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-α-substituted α,β-diamino acid derivatives with a high level control of chemo-, diastereo-, and enantioselectivity.

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Key Words

Multicomponent Reaction, Mannich Reaction, α-amino acids, β-amino acids


ID: J48-Y2011-1630