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Catalytic Asymmetric Michael Reactions of α,β-Unsaturated Ketones with Sulfonyl-Containing Nucleophiles: Chiral Synthesis of (R)-Muscone and (S)-Celery Ketone

Authors

  • Xiaomin Sun,

    1. Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-64251830
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  • Feng Yu,

    1. Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-64251830
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  • Tingting Ye,

    1. Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-64251830
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  • Prof. Dr. Xinmiao Liang,

    1. Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-64251830
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  • Prof. Dr. Jinxing Ye

    Corresponding author
    1. Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-64251830
    • Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-64251830
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Abstract

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An amine worth its salt: A highly enantioselective Michael addition reaction of α,β-unsaturated ketones with the sulfonyl-containing nucleophiles bis(phenylsulfonyl)methane and 1-(phenylsulfonyl)propan-2-one, catalyzed by a chiral primary amine salt, has been developed and gives excellent enantioselectivities (see scheme). The methodology has successfully demonstrated its synthetic utility in the chiral synthesis of (R)-muscone and (S)-celery ketone.

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