Get access

Catalytic Asymmetric Synthesis of Aromatic Spiroketals by SpinPhox/Iridium(I)-Catalyzed Hydrogenation and Spiroketalization of α,α′-Bis(2-hydroxyarylidene) Ketones

Authors

  • Xiaoming Wang,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
    Search for more papers by this author
  • Dr. Zhaobin Han,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
    Search for more papers by this author
  • Dr. Zheng Wang,

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
    Search for more papers by this author
  • Prof. Dr. Kuiling Ding

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
    Search for more papers by this author

  • We thank the National Natural Science Foundation of China (grant nos. 20821002, 20923005, 20972176), the Major Basic Research Development Program of China (grant no. 2010CB833300), the Chinese Academy of Sciences, and the Science and Technology Commission of Shanghai Municipality for the financial support of this work.

Abstract

original image

From spiro to spiro: An iridium(I) complex with a spiral P,N ligand (SpinPhox) is highly efficient in the catalytic asymmetric hydrogenation of α,α′-bis(2-hydroxyarylidene) ketones to afford the corresponding aromatic spiroketals in high yields with excellent diastereo- and enantioselectivities (see scheme). The complex plays a dual role in the reaction, acting as catalyst for both the hydrogenation of C[DOUBLE BOND]C bonds and the subsequent spiroketalization of bisphenolic ketones.

Ancillary