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Paper | Special issue | Vol 88, No. 2, 2014, pp.1355-1370
Published online, 11th September, 2013
DOI: 10.3987/COM-13-S(S)105
Enantioselective Synthesis of Planar-Chiral Phosphines with 1,N-Dioxa[N]paracyclophane Scaffold and Their Application as Chiral Ligands

Kazumasa Kanda, Shoya Oshima, Tsubasa Shizuno, Risa Hamanaka, Miku Fukai, and Takanori Shibata*

*Chemistry and Biochemistry, Advanced Research Center of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


A new family of chiral phosphines based on planar-chiral 1,n-dioxa[n]paracyclophane scaffold was created. They were synthesized with excellent enantioselectivity via asymmetric ortho-lithiation using sec-butyllithium and (-)-sparteine. These phosphines were used as chiral ligands in three reactions: Ag-catalyzed allylation of imines, Pd-catalyzed asymmetric Sonogashira coupling of diiodoparacyclophanes, and Pd-catalyzed asymmetric Suzuki-Miyaura coupling of tricarbonyl(η6-ortho-dichlorobenzene)chromium.