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Catalytic Asymmetric Bromoamination of Chalcones: Highly Efficient Synthesis of Chiral α-Bromo-β-Amino Ketone Derivatives

Authors

  • Yunfei Cai,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Xiaohua Liu Dr.,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Yonghai Hui,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Jun Jiang,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Wentao Wang,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Weiliang Chen,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Lili Lin Dr.,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Xiaoming Feng Prof. Dr.

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • We appreciate the financial support from the National Natural Science Foundation of China (Nos. 20732003 and 20872097), the PCSIRT (No. IRT0846), and the National Basic Research Program of China (973 Program; No. 2010CB833300). We also thank Sichuan University Analytical & Testing Center for NMR analysis.

Abstract

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Stand and deliver: The first highly regio- and enantioselective bromoamination of chalcones has been developed which proceeds via an unusual bromonium-based mechanism to deliver the title compounds. Excellent results were obtained using 0.05 mol % of the C2-symmetric N,N′-dioxide/scandium(III) complex under mild conditions (see scheme).

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