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Synthesis of Pyridyl-dihydrobenzooxaphosphole Ligands and Their Application in Asymmetric Hydrogenation of Unfunctionalized Alkenes

2014; American Chemical Society; Volume: 79; Issue: 3 Linguagem: Inglês

10.1021/jo4024864

1520-6904

Bo Qu, Lalith P. Samankumara, Jolaine Savoie, Daniel R. Fandrick, Nizar Haddad, Xudong Wei, Shengli Ma, Heewon Lee, Sonia Rodrı́guez, Carl A. Busacca, Nathan K. Yee, Jinhua J. Song, Chris H. Senanayake,

Asymmetric Synthesis and Catalysis

Synthesis of the electron-rich 2-substituted-6-(phenylsulfonyl)pyridines is presented. A series of air-stable, tunable, P-chiral pyridyl-dihydrobenzooxaphosphole ligands were designed and synthesized by a diastereoselective SNAr substitution of the corresponding sulfonyl pyridines. The ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes with good enantioselectivities.