Enantioselective Synthesis of Highly Functionalized Phosphonate-Substituted Pyrans or Dihydropyrans Through Asymmetric [4+2] Cycloaddition of β,γ-Unsaturated α-Ketophosphonates with Allenic Esters

Authors

  • Dr. Cheng-Kui Pei,

    1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237 (China)
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  • Yu Jiang,

    1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237 (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 (China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)
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  • Prof. Dr. 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 (China)
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)
    • Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237 (China)
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  • We thank the Shanghai Municipal Committee of Science and Technology (11JC1402600), the National Basic Research Program of China (973)-2010CB833302, and the National Natural Science Foundation of China for financial support (21072206, 20472096, 20872162, 20672127, 21121062 and 20732008).

Abstract

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Tell me which you want: Catalytic asymmetric [4+2] cycloadditions of β,γ-unsaturated α-ketophosphonates with allenic esters catalyzed by organocatalysts derived from different cinchona alkaloids have been developed, affording phosphonate-substituted functionalized pyran and dihydropyran derivatives in excellent yields with high enantioselectivities under mild conditions. The choice of product is controlled by the hydrogen bonding characteristics of the chosen catalyst.

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