Phosphine-Catalyzed Asymmetric Formal [4+2] Tandem Cyclization of Activated Dienes with Isatylidenemalononitriles: Enantioselective Synthesis of Multistereogenic Spirocyclic Oxindoles

Authors

  • Fang-Le Hu,

    1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, People's Repuiblic of China
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  • Yin Wei,

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China, Fax: (+86)-21-6416-6128
    • Yin Wei, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China, Fax: (+86)-21-6416-6128

      Min Shi, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, People's Repuiblic of China

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  • Min Shi

    Corresponding author
    1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, People's Repuiblic of China
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China, Fax: (+86)-21-6416-6128
    • Yin Wei, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China, Fax: (+86)-21-6416-6128

      Min Shi, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, People's Repuiblic of China

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Abstract

The first highly enantioselective formal [4+2] tandem cyclizations between isatylidenemalononitriles and activated dienes catalyzed by bifunctional chiral phosphine catalysts have been developed, yielding multistereogenic spirocyclic oxindoles in high yields and excellent optical purity. This reaction is accomplished via a tandem Rauhut–Currier/Michael/Rauhut–Currier reaction sequence.

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