Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles

• Dingqiao Yang,
• Ping Hu,
• Yuhua Long,
• Yujuan Wu,
• Heping Zeng,
• Hui Wang and
• Xiongjun Zuo

Beilstein J. Org. Chem. 2009, 5, No. 53, doi:10.3762/bjoc.5.53

• and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography. Keywords: chiral bisphosphine ligand; iridium catalyst; oxabicyclic alkenes; ring-opening reaction; Introduction Substituted dihydronaphthalenes are important molecules with

• molecules with the dihydronaphthalene skeleton. Results and Discussion The ARO reaction involves many components of the chemical agents; we first attempted to optimize the ligand to iridium catalyst system (Scheme 1). In our initial experiments, we chose an achiral 1,1′-bis(diphenylphosphino)ferrocene (DPPF

• order of Firidium catalyst from chloride to iodide or bromide leads to improvements in