Organocatalytic Asymmetric Inverse-Electron-Demand Aza-Diels–Alder Reaction of N-Sulfonyl-1-aza-1,3-butadienes and Aldehydes

Authors

  • Bo Han,

    1. Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609
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  • Jun-Long Li,

    1. Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609
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  • Chao Ma,

    1. Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609
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  • Shan-Jun Zhang,

    1. Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609
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  • Ying-Chun Chen Prof. Dr.

    1. Key Laboratory of Drug Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28 85502609
    2. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)
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Abstract

original image

Wasser ist entscheidend, um die Titelreaktion in Gegenwart des α,α-Diphenylprolinols 1 mit hohen Umsätzen ablaufen zu lassen. Ein breites Spektrum an Substraten wurde mit sehr guten Stereoselektivitäten umgesetzt (TMS=Trimethylsilyl, Tos=p-Toluolsulfonyl). Die entstehenden Halbaminale konnten in eine Vielzahl chiraler Piperidine und andere wertvolle Verbindungen überführt werden.

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