A bisphosphepine ligand with stereogenic phosphorus centers for the practical synthesis of β-aryl-β-amino acids by asymmetric hydrogenation

Angewandte Chemie - International Edition

Volumn 42, Issue 30, 2003, Pages 3509-3511

  Tang, Wenjun ^a   Wang, Weimin ^a   Chi, Yongxiang ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Asymmetric synthesis; Hydrogenation; Ligand design; P ligands; Rhodium

Indexed keywords

CATALYSTS; HYDROGENATION; PHOSPHORUS; SYNTHESIS (CHEMICAL);

LIGANDS;

AMINO ACIDS;

BETA AMINO ACID; BISPHOSPHEPINE; PHOSPHORUS; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; DERIVATIZATION; ENANTIOMER; HYDROGENATION; LIGAND BINDING; STOICHIOMETRY; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; CATALYSIS; HYDROGENATION; LIGANDS; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHORUS; RHODIUM; STEREOISOMERISM;

EID: 0042531839     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351465     Document Type: Article

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34. Several binaphthophosphepine ligands in which the P atoms are not stereogenic centers have been reported; see: a) D. Xiao, Z. Zhang, X. Zhang, Org. Lett. 1999, 1, 1679-1681; b) D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533-3536; c) Y. Chi, X. Zhang, Tetrahedron Lett. 2002, 43, 4849-4852;d) K. Junge, G. Oehme, A. Monsees, T. Riermeier, U. Dingerdissen, M. Beller, Tetrahedron Lett. 2002, 43, 4977-4980.
35. Several binaphthophosphepine ligands in which the P atoms are not stereogenic centers have been reported; see: a) D. Xiao, Z. Zhang, X. Zhang, Org. Lett. 1999, 1, 1679-1681; b) D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533-3536; c) Y. Chi, X. Zhang, Tetrahedron Lett. 2002, 43, 4849-4852;d) K. Junge, G. Oehme, A. Monsees, T. Riermeier, U. Dingerdissen, M. Beller, Tetrahedron Lett. 2002, 43, 4977-4980.
36. Several binaphthophosphepine ligands in which the P atoms are not stereogenic centers have been reported; see: a) D. Xiao, Z. Zhang, X. Zhang, Org. Lett. 1999, 1, 1679-1681; b) D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533-3536; c) Y. Chi, X. Zhang, Tetrahedron Lett. 2002, 43, 4849-4852;d) K. Junge, G. Oehme, A. Monsees, T. Riermeier, U. Dingerdissen, M. Beller, Tetrahedron Lett. 2002, 43, 4977-4980.
37. Several binaphthophosphepine ligands in which the P atoms are not stereogenic centers have been reported; see: a) D. Xiao, Z. Zhang, X. Zhang, Org. Lett. 1999, 1, 1679-1681; b) D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533-3536; c) Y. Chi, X. Zhang, Tetrahedron Lett. 2002, 43, 4849-4852;d) K. Junge, G. Oehme, A. Monsees, T. Riermeier, U. Dingerdissen, M. Beller, Tetrahedron Lett. 2002, 43, 4977-4980.
38. CCDC-204741 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+ 44)1223-336-033; or depost@ccdc.cam.ac.uk). We thank Dr. H. Yennawar for solving the crystal structure.
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43. See Supporting Information for details.
44. No reaction was observed in the absence of acid. HBF4 was used to protonate the pyridine nitrogen atom. A similar strategy was applied in the hydrogenation of pyridyl α-dehydroamino acid derivatives; see: C. Döbler, H.-J. Kreuzfeld, M. Michalik, H. W. Krause, Tetrahedron: Asymmetry 1996, 7, 117-125.
45. The Supporting Information includes procedures for the synthesis of and analytical data for binapine, procedures for the synthesis of substrates, hydrogenation procedures, information on molecular simulation, and the X-ray crystal structure of 3.