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Development of New P-Chiral P,π-Dihydrobenzooxaphosphole Hybrid Ligands for Asymmetric Catalysis

Joshua D. Sieber*, Divya Chennamadhavuni, Keith R. Fandrick, Bo Qu, Zhengxu S. Han, Jolaine Savoie, Shengli Ma, Lalith P. Samankumara, Nelu Grinberg, Heewon Lee, Jinhua J. Song, and Chris H. Senanayake

*Department of Chemical Development, Boehringer Ingelheim Phamaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States, Email:

J. D. Sieber, D. Chennamadhavuni, K. R. Fandrick, B. Qu, Z. S. Han, J. Savoie, S. Ma, L. P. Samankumara, N. Grinberg, H. Lee, J. J. Song, C. H. Senanayake, Org. Lett., 2014, 16, 5494-5497.

DOI: 10.1021/ol5027798 (free Supporting Information)


P-chiral P,π-hybrid ligands are both sterically and electronically tunable at the substituents on the phosphorus atom and the π-system of the ligand. Catalytic asymmetric addition of boronic acids to imines proceeds with high levels of enantioinduction in the presence of these ligands.

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ID: J54-Y2014