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Lipase-Catalyzed Stereoselective Cross-Aldol Reaction Promoted by Water

Authors

  • Zong-Bo Xie,

    1. Key Laboratory of Green Chemistry and Technology (Ministry of Education) and State Key Laboratory of Oral Diseases, College of Chemistry, Sichuan University, No.29 Wangjiang Road, Chengdu, 610064 (P.R. China), Fax: (+86) 28-85415886
    2. School of Chemistry, Biology and Material Science, East China Institute of Technology, No.56 Xuefu Road, Fuzhou, 344000 (P.R. China), Fax: (+86) 794-8258320
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  • Dr. Na Wang,

    Corresponding author
    1. Key Laboratory of Green Chemistry and Technology (Ministry of Education) and State Key Laboratory of Oral Diseases, College of Chemistry, Sichuan University, No.29 Wangjiang Road, Chengdu, 610064 (P.R. China), Fax: (+86) 28-85415886
    • Key Laboratory of Green Chemistry and Technology (Ministry of Education) and State Key Laboratory of Oral Diseases, College of Chemistry, Sichuan University, No.29 Wangjiang Road, Chengdu, 610064 (P.R. China), Fax: (+86) 28-85415886

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  • Long-Hua Zhou,

    1. Key Laboratory of Green Chemistry and Technology (Ministry of Education) and State Key Laboratory of Oral Diseases, College of Chemistry, Sichuan University, No.29 Wangjiang Road, Chengdu, 610064 (P.R. China), Fax: (+86) 28-85415886
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  • Fang Wan,

    1. Key Laboratory of Green Chemistry and Technology (Ministry of Education) and State Key Laboratory of Oral Diseases, College of Chemistry, Sichuan University, No.29 Wangjiang Road, Chengdu, 610064 (P.R. China), Fax: (+86) 28-85415886
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  • Ting He,

    1. Key Laboratory of Green Chemistry and Technology (Ministry of Education) and State Key Laboratory of Oral Diseases, College of Chemistry, Sichuan University, No.29 Wangjiang Road, Chengdu, 610064 (P.R. China), Fax: (+86) 28-85415886
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  • Prof. Dr. Zhang-Gao Le,

    1. School of Chemistry, Biology and Material Science, East China Institute of Technology, No.56 Xuefu Road, Fuzhou, 344000 (P.R. China), Fax: (+86) 794-8258320
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  • Prof. Dr. Xiao-Qi Yu

    Corresponding author
    1. Key Laboratory of Green Chemistry and Technology (Ministry of Education) and State Key Laboratory of Oral Diseases, College of Chemistry, Sichuan University, No.29 Wangjiang Road, Chengdu, 610064 (P.R. China), Fax: (+86) 28-85415886
    • Key Laboratory of Green Chemistry and Technology (Ministry of Education) and State Key Laboratory of Oral Diseases, College of Chemistry, Sichuan University, No.29 Wangjiang Road, Chengdu, 610064 (P.R. China), Fax: (+86) 28-85415886

    Search for more papers by this author

Abstract

PPL, lipase from porcine pancreas, is first reported to catalyze direct asymmetric aldol reactions between aromatic aldehydes and cyclic ketones. More importantly, the catalytic activity of PPL was greatly promoted by a small quantity of water at 37 °C. A wide range of aromatic aldehydes reacted with cyclic ketones to provide the corresponding aldol products with high yields (up to 99 %) and moderate to good stereoselectivity (up to 90 % ee and 99:1 dr).

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