Developing a new class of axial chiral phosphorus ligands: Preparation and characterization of enantiopure atropisomeric phosphinines

Chemistry - A European Journal

Volumn 14, Issue 16, 2008, Pages 4899-4905

  Müller, Christian ^a   Pidko, Evgeny A ^a   Staring, Antonius J P M ^a   Lutz, Martin ^b   Spek, Anthony L ^b   Van Santen, Rutger A ^a   Vogt, Dieter ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Atropisomerism; Chirality; Density functional calculations; Phosphinines; Phosphorus heterocycles

Indexed keywords

CHIRALITY; CHROMATOGRAPHIC ANALYSIS; PHOSPHORUS;

ATROPISOMERISM; DENSITY FUNCTIONAL CALCULATIONS; PHOSPHININES; PHOSPHORUS HETEROCYCLES;

ENANTIOMERS;

BENZENE DERIVATIVE; LIGAND; ORGANOPHOSPHORUS COMPOUND; PHOSPHININE; PHOSPHORUS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

BENZENE DERIVATIVES; CRYSTALLOGRAPHY, X-RAY; KINETICS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHORUS; STEREOISOMERISM;

EID: 53849089946     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800175     Document Type: Article

References (50)

1. a) G. Märkl, Angew. Chem. 1966, 78, 907-908;
2. Angew. Chem. Int. Ed. Engl. 1966, 5, 846-847.;
3. b) A. J. Ashe III, J. Am. Chem. Soc. 1971, 93, 3293-3295.
4. For recent reviews, see: a) C. Müller, D. Vogt, Dalton Trans. 2007, 5505-5523;
5. b) P. Le Floch, Coord. Chem. Rev. 2006, 250, 627-681;
6. c) F. Malhey, P. Le Floch, Science of Synthesis 2005, 15, 1097-1155;
7. d) F. Malhey, Angew. Chem. 2003, 115, 1616-1643;
8. Angew. Chem. Int. Ed. 2003, 42, 1578-1604;
9. e) P. Le Floch, F. Mathey, Coord. Chem. Rev. 1998, 179-180, 771-791.
10. a) P. Le Floch in Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain, (Ed.: F. Mathey), Pergamon, Palaiseau, 2001, pp. 485-533;
11. b) G. Märkl in Multiple Bonds and Low Coordination in Phosphorus Chemistry, (Eds.: M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990, p. 220.
12. a) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics 1996, 15, 2713-2719;
13. b) B. Breit, Chem. Commun. 1996, 2071-2072;
14. c) B. Breit, J. Mol. Catal. A 1999, 143, 143-154;
15. d) B. Breit, R. Winde, K. Harms, J. Chem. Soc. Perkin Trans. 1 1997, 18, 2681-2682;
16. e) B. Breit, R. Winde, T. Mackewitz, R. Paciello, K. Harms, Chem. Eur. J. 2001, 7, 3106-3121;
17. f) L. Weber, Angew. Chem. 2002, 114, 583-592;
18. Angew. Chem. Int. Ed. 2002, 41, 563-572;
19. g) M. T. Reetz, G. Mehler, Tetrahedron Lett. 2003, 44, 4593-4596;
20. h) M. T. Reetz, X. Li, Angew. Chem. 2005, 117, 3022-3024;
21. Angew. Chem. Int. Ed. 2005, 44, 2962-2964;
22. i) C. Müller, L. Guarrotxena-Lopéz, H. Kooijman, A. L. Spek, D. Vogt, Tetrahedron Lett. 2006, 47, 2017-2020.
23. a) C. Müller, M. Lutz, A. L. Spek, D. Vogt, J. Chem. Crystallogr. 2006, 36(12), 869-874;
24. b) C. Müller, D. Wasserberg, J. J. M. Weemers, E. A. Pidko, S. Hoffmann, M. Lutz, A. L. Spek, S. C. J. Meskers, R. A. J. Janssen, R. A. van Santen, D. Vogt, Chem. Eur. J. 2007, 13, 4548-4559;
25. c) C. Müller, Z. Freixa, M. Lutz, A. L. Spek, D. Vogt, P. W. N. M. van Leeuwen, Organometallics 2008, 27, 834-838.
26. C. Müller, E. A. Pidko, M. Lutz, A. L. Spek, R. A. van Santen, D. Vogt, Dalton Trans. 2007, 5372-5375.
27. For related atropisomeric pyridines, see: a) A. Gutnov, B. Heller, C. Fischer, H.-J. Drexler, A. Spannenberg, B. Sundermann, C. Sundermann, Angew. Chem. 2004, 116, 3883-3886;
28. Angew. Chem. Int. Ed. 2004, 43, 3795-3797;
29. b) B. Heller, A. Gutnov, C. Fischer, H.-J. Drexler, A. Spannenberg, D. Redkin, C. Sundermann, B. Sundermann, Chem. Eur. J. 2007, 13, 1117-1128.
30. G. Bringmann, A. J. Price Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518-5563;
31. Angew. Chem. Int. Ed. 2005, 44, 5384-5427.
32. A. Shiozawa, K. Narita, G. Izumi, S. Kurashige, K. Sakitama, M. Ishikawa, Eur. J. Med. Chem. 1995, 30, 85-94.
33. S. M. M. Elshafie, J. Prakt. Chemie 1982, 324, 149-154.
34. J. W. Ellis, K. N. Harrison, P. A. T. Hoye, A. G. Orpen, P. G. Pringle, M. B. Smith, Inorg. Chem. 1992, 31, 3026-3033.
35. a) S. Funda Oǧuz, İ. Doǧan, Tetrahedron: Asymmetry 2003, 14, 1857-1864;
36. b) M. T. Harju, P. Haglund, Fresenius J. Anal. Chem. 1999, 364, 219-223.
37. a) K. Cabrera, M. Jung, M. Fluck, V. Schurig, J. Chromatogr. A 1996, 731, 315-321;
38. b) R. J. Friary, M. Spangler, R. Osterman, L. Schulman, J. H. Schwerdt, Chirality 1996, 8, 364-371.
39. The errors for k, ΔG, and τ were determined by assuming an estimated error of 1 % for the integrated areas of the HPLC chromatogram.
40. K. Dimroth, Fortschr. Chem. Forsch. 1973, 38, 1-147.
41. G. Märkl, 20 Jahre Fonds der Chemischen Industrie. Verband der Chemischen Industrie, Frankfurt, 1970, p. 113.
42. a) Circular Dichroism: Principles and Applications, (Eds.: K. Nakanishi, N. Berova, R. W. Woody), VCH, Weinheim, 1994;
43. b) D. Casarini, L. Lunazzi, M. Mancinelli, A. Mazzanti, C. Rosini, J. Org. Chem. 2007, 72, 7667-7676;
44. c) T. Mori, Y. Inoue, S. Grimme, J. Phys. Chem. A 2007, 111, 4222-4234;
45. d) F. Ceccacci, G. Mancini, P. Mencarelli, C. Villani, Tetrahedron: Asymmetry 2003, 14, 3117-3122;
46. e) N. Harada, A. Saito, N. Koumura, H. Uda, B. de Lange, W. F. Jager, H. Wynberg, B. L. Feringa, J. Am. Chem. Soc. 1997, 119, 7241-7248.
47. G. M. Sheldrick, SADABS: Area-Detector Absorption Correction, v2.10, Universität Göltingen, Götlingen (Germany), 1999.
48. G. M. Sheldrick, Acta Cryst. 2008, A64, 112-122.
49. A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.
50. Gaussian 03, Revision B.05, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. lshida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.