Synlett

Mannich Reaction of Imines and Silyl Enol Ethers Induced by Radical Cation Salts: Synthesis of β-Amino Ketones

X Jia, W Wang, Z Quan, Y Ren, X Wang

Index: Jia, Xiao-Dong; Wang, Wen-Juan; Huo, Cong-De; Quan, Zheng-Jun; Ren, Yan; Wang, Xi-Cun Synlett, 2010 , # 19 p. 2964 - 2968

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Citation Number: 4

Abstract

Abstract Mannich reaction of imines and sily enol ethers induced by radical cation salts was investigated and a series of β-amino ketones were synthesized. Reverse diastereoselectivity was obtained in the reactions of imines and silyl enol ethers of pentan-2-one and pentan-3- one, respectively, which was rationalized by quantum mechanical calculations. A single electron-transfer mechanism was proposed in which the imine radical cation acts as an ...

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