The stereodynamics of 5,5'-disubstituted BIPHEPs

Chirality

Volumn 25, Issue 2, 2013, Pages 126-132

  Maier, Frank ^a   Trapp, Oliver ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

BIPHEP; dynamic HPLC; interconversion barrier; kinetics; unified equation

Indexed keywords

BIPHENYL DERIVATIVE; HYDROXYL GROUP; LIGAND; METHYL GROUP;

ACCURACY; ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; ENERGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; SUBSTITUTION REACTION; TEMPERATURE DEPENDENCE;

EID: 84872833918     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22125     Document Type: Article

References (43)

1. Noyori R,. Asymmetric catalysis: science and opportunities. Adv Synth Catal 2003; 345: 15-32.
2. Mikami K, Aikawa K, Yusa Y, Jodry JJ, Yamanaka M,. Tropos or atropos? That is the question! Synlett 2002; 10: 1561-1578.
3. Mikami K, Korenaga T, Terada M, Ohkuma T, Pham T, Noyori R,. Konformativ flexible Biphenyl-Phosphanliganden für Ru-katalysierte enantioselektive Hydrierungen. Angew Chem 1999; 111: 517-519
4. Conformationally flexible biphenylphosphane ligands for Ru-catalyzed enantioselective hydrogenation. Angew Chem Int Ed 1999; 38: 495-497.
5. Mikami K, Aikawa K, Yusa Y,. Asymmetric activation of the Pd catalyst bearing the tropos biphenylphosphine (BIPHEP) ligand with the chiral diaminobinaphthyl (DABN) activator. Org Lett 2002; 4: 95-97.
6. Aikawa K, Kojima M, Mikami K,. Axial chirality control of gold(BIPHEP) complexes by chiral anions: application to asymmetric catalysis. Angew Chem Int Ed 2009; 48: 6073-6077.
7. Kojima M, Mikami K,. Enantioselective intramolecular hydroamination of N-alkenyl ureas catalyzed by tropos BIPHEP-Gold(I) complexes with Au-Au interaction. Synlett 2012; 23: 57-61.
8. Kojima M, Mikami K,. Enantioselective intermolecular carbon-carbon bond formation of glyoxylate imines with allylstannanes catalyzed by tropos BIPHEP-Gold(I) complexes with Au-Au interactions. Chem Eur J 2011; 17: 13950-13953.
9. Punniyamurthy T, Mayr M, Dorofeev AS, Bataille CJR, Gosiewska S, Nguyen B, Cowley AR, Brown JM,. Enantiomerically pure bicyclo[3.3.1]nona-2,6-diene as the sole source of enantioselectivity in BIPHEP-rh asymmetric hydrogenation. Chem Commun 2008; 5092-5094.
10. Noyori R, Ikeda T, Ohkuma T, Widhalm M, Kitamura M, Takaya H, Akutagawa S, Sayo N, Saito T,. Stereoselective hydrogenation via dynamic kinetic resolution. J Am Chem Soc 1989; 111: 9134-9135.
11. Gasparrini F, Misiti D, Pierini M, Villani C,. Enantiomerization barriers by dynamic HPLC. Stationary phase effects. Tetrahedron: Asymmetry 1997; 8: 2069-2073.
12. Trapp O, Schoetz G, Schurig V,. Determination of enantiomerization barriers by dynamic and stopped flow chromatographic methods. Chirality 2001; 13: 403-414.
13. Gasparrini F, D'Acquarica I, Pierini M, Villani C,. Chromatographic resolution and enantiomerization barriers of axially chiral 1-naphthamides. J Sep Sci 2001; 24: 941-946.
14. Trapp O, Caccamese S, Schmidt C, Böhmer V, Schurig V,. Enantiomerization of an inherently chiral resorcarene derivative: determination of the interconversion barrier by computer simulation of the dynamic HPLC experiment. Tetrahedron: Asymmetry 2001; 12: 1395-1398.
15. Trapp O, Trapp G, Schurig V,. Direct calculation and computer simulation of the enantiomerization barrier of oxazepam in dynamic HPLC experiments-a comparative study. J Biochem Biophys Methods 2002; 54: 301-313.
16. D'Acquarica I, Gasparrini F, Pierini M, Villani C, Zappia G,. Dynamic HPLC on chiral stationary phases: a powerful tool for the investigation of stereomutation processes. J Sep Sci 2006; 29: 1508-1516.
17. Wolf C,. Stereolabile chiral compounds: analysis by dynamic chromatography and stopped-flow methods. Chem Soc Rev 2005; 34: 595-608.
18. Wolf C,. Dynamic stereochemistry of chiral compounds-principles and applications. Cambridge: RSC Publishing; 2008.
19. Ciogli A, Bicker W, Lindner W,. Determination of enantiomerization barriers of hypericin and pseudohypericin by dynamic high-performance liquid chromatography on immobilized polysaccharide-type chiral stationary phases and off-column racemization experiments. Chirality 2010; 22: 463-471.
20. Maier F, Trapp O,. Quantifizierung der Stationärphasen- und Lösungsmitteleinflüsse auf die Stereodynamik von BIPHEP-Liganden durch dynamische Drei- Säulen-HPLC. Angew Chem 2012; 124: 3039-3043
21. Effects of the stationary phase and the solvent on the stereodynamics of BIPHEP ligands quantified by dynamic three-column HPLC. Angew Chem Int Ed 2012; 51: 2985-2988.
22. Wolf C, König WA, Roussel C,. Influence of substituents on the rotational energy barrier of atropisomeric biphenyls-studies by polarimetry and dynamic gas chromatography. Liebigs Ann 1995; 781-786.
23. Wolf C, König WA, Roussel C,. Conversion of a racemate into a single enantiomer in one step by chiral liquid chromatography: studies with rac-2,2'-diiodobiphenyl. Chirality 1995; 7: 610-611.
24. Wolf C, Hochmuth DH, König WA, Roussel C,. Influence of substituents on the rotational energy barrier of atropisomeric biphenyls II. Liebigs Ann 1996; 357-363.
25. Ceccacci F, Mancini G, Mencarelli P, Villani C,. Determination of the rotational barrier of a chiral biphenyl: comparison of theoretical and experimental data. Tetrahedron: Asymmetry 2003; 14: 3117-3122.
26. Soai K, Shibata T, Morioka H, Choji K,. Asymmetric autocatalysis and amplification of enantiomeric execss of a chiral molecule. Nature 1995; 378: 767-768.
27. Shibata T, Yonekubo S, Soai K,. Eine nahezu ideale asymmetrische autokatalyse mit (2-alkinyl-5-pyrimidyl)alkanolen. Angew Chem 1999; 111: 746-748
28. Practically perfect asymmetric autocatalysis with (2-alkynyl-5-pyrimidyl) alkanols. Angew Chem Int Ed 1999; 38: 659-661.
29. Liang Y, Wang Z, Ding K,. Generation of self-supported Noyori-type catalysts using achiral bridged-BIPHEP for heterogeneous asymmetric hydrogenation of ketones. Adv Synth Catal 2006; 348: 1533-1538.
30. Wang C, Yang G, Zhuang J, Zhang W,. From tropos to atropos: 5,5'-bridged 2,2'-bis(diphenylphosphino)biphenyls as chiral ligands for highly enantioselective palladium-catalyzed hydrogenation of α-phthalimide ketones. Tetrahedron Lett 2010; 51: 2044-2047.
31. Trapp O,. Unified equation for access to rate constants of first-order reactions in dynamic and on-column reaction chromatography. Anal Chem 2006; 78: 189-198.
32. Trapp O,. Fast and precise access to enantiomerization rate constants in dynamic chromatography. Chirality 2006; 18: 489-497.
33. Trapp O, Sahraoui L, Hofstadt W, Könen W,. The stereodynamics of 1,2-dipropyldiaziridines. Chirality 2010; 22: 284-291.
34. Trapp O,. The unified equation for the evaluation of degenerated first order reactions in dynamic electrophoresis. Electrophoresis 2006; 27: 2999-3006.
35. Trapp O,. The unified equation for the evaluation of first order reactions in dynamic electrophoresis. Electrophoresis 2006; 27: 534-541.
36. Trapp O,. A novel software tool for high throughput measurements of interconversion barriers: DCXplorer. J Chromatogr B 2008; 875: 42-47.
37. Trapp O, Bremer S, Weber SK,. Accessing reaction rate constants in on-column reaction chromatography: an extended unified equation for reaction educts and products with different response factors. Anal Bioanal Chem 2009; 395: 1673-1679.
38. Bürkle W, Karfunkel H, Schurig V,. Dynamic phenomena during enantiomer resolution by complexation gas chromatography. J Chromatogr 1984; 288: 1-14.
39. Trapp O, Schurig V,. Stereointegrity of Tröger's base: gas-chromatographic determination of the enantiomerization barrier. J Am Chem Soc 2000; 122: 1424-1430.
40. Trapp O, Schurig V,. Chromwin-a computer program for the determination of enantiomerization barriers in dynamic chromatography. Comput Chem 2001; 25: 187-195.
41. Trapp O,. The unified equation for the evaluation of first order reactions in dynamic electrophoresis. Electrophoresis 2006; 27: 534-541.
42. Rieger M, Westheimer H,. The calculation and determination of the buttressing effect for the racemization of 2,2', 3,3'-tetraiodo-5,5'- dicarboxybiphenyl. J Am Chem Soc 1950; 72: 19-28.
43. Dunitz JD,. Win some, lose some: enthalpy-entropy compensation in weak intermolecular interactions. Chem Biol 1995; 2: 709-712.