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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: joshua.sieberboehringer-ingelheim.com

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)


Abstract

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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Key Words

diarylmethylamines


ID: J54-Y2014