Asymmetric Synthesis of 2,3-Dihydroquinolin-4-one Derivatives Catalyzed by a Chiral Bisguanidium Salt

Authors

  • Xiao Xiao,

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

    Corresponding author
    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (P.R. China), Fax: (+86) 28-8541-8249
    • Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (P.R. China), Fax: (+86) 28-8541-8249
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  • Shunxi Dong,

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

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

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

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

original image

Worth its salt: An orgnaocatalytic asymmetric intramolecular aza-Michael reaction and one-pot bromination reaction of activated α,β-unsaturated ketones have been realized using a chiral bisguanidium salt (see scheme). Optically enriched 2-aryl- and 2-alkyl-substituted dihydroquinones and brominated dihydroquinones could be obtained (up to 99 % yield and 99 % ee for the aza-Michael reaction; and up to 95 % yield, 96:4 d.r., and 95 % ee for the bromination reaction).

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