Application of phosphine-phosphite ligands in the iridium catalyzed enantioselective hydrogenation of 2-Methylquinoline

Molecules

Volumn 15, Issue 11, 2010, Pages 7732-7741

  Rubio, Miguel ^a   Pizzano, Antonio ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

Asymmetric hydrogenation; Chiral ligands; Iridium; Phosphines; Phosphites; Quinolines

Indexed keywords

2-METHYLQUINOLINE; IRIDIUM; PHOSPHINE; PHOSPHINE DERIVATIVE; PHOSPHITE; QUINALDINE; QUINALDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

CATALYSIS; HYDROGENATION; IRIDIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHOSPHINES; PHOSPHITES; QUINALDINES; STEREOISOMERISM;

EID: 78649509155     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15117732     Document Type: Article

References (35)

1. Tang, W.; Zhang, X. New chiral phosphorus ligands for asymmetric hydrogenation. Chem. Rev. 2003, 103, 3029-3070.
2. Bell, S.; Wustenberg, B.; Kaiser, S.; Menges, F.; Netscher, T.; Pfaltz, A. Asymmetric hydrogenation of unfunctionalized, purely alkyl-substituted olefins. Science 2006, 311, 642-644.
3. Cui, X.H.; Ogle, J.W.; Burgess, K. Stereoselective hydrogenations of aryl-substituted dienes. Chem. Comm. 2005, 672-674.
4. Hoge, G.; Wu, H.-P.; Kissel, W.S.; Pflum, D.A.; Greene, D.J.; Bao, J. Highly selective asymmetric hydrogenation using a three hindered quadrant bisphosphine rhodium catalyst. J. Am. Chem. Soc. 2004, 126, 5966-5967.
5. Evans, D.A.; Campos, K.R.; Tedrow, J.S.; Michael, F.E.; Cagne, M.R. Application of chiral mixed phosphorus/sulfur ligands to enantioselective rhodium-catalyzed dehydroamino acid hydrogenation and ketone hydrosilylation processes J. Am. Chem. Soc. 2003, 125, 3534-3543.
6. Keay, J.D. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Volume 8, pp. 579-601.
7. Wang, D.-W.; Zhou, Y.-G.; Chen, Q.-A.; Wang, D.-S. In Chiral Amine Synthesis: Methods, Developments and Applications; Nugent, T.C., Ed.; Wiley-VCH: Weinheim, 2010; pp. 299-339.
8. Barton, D.H.R., Nakanishi, K., Meth-Cohn, O., Eds; Comprehensive Natural Products Chemistry; Elsevier: Oxford, 1999; Vol. 1-9.
9. Jacquemond-Collet, I.; Hannedouche, S.; Fabre, N.; Fouraste, I.; Moulis, C. Two tetrahydroquinoline alkaloids from Galipea officinalis. Phytochemistry 1999, 51, 1167-1169.
10. Rokotoson, J.H.; Fabre, N.; Jacquemond-Collet, I.; Hannedouche, S.; Fabre, N.; Fouraste, I.; Moulis, C. Alkaloids from Galipea officinalis. Planta Med. 1998, 64, 762-763.
11. Houghton, P.J.; Woldemariam, T.Z.; Watanabe, Y.; Yates, M. Activity against Mycobacterium tuberculosis of alkaloid constituents of angostura black, Galipea officinalis. Planta Med. 1999, 65, 250-254.
12. Jacquemond-Collet, I.; Bessiere, J.M.; Hannedouche, S.; Bertrand, C.; Fouraste, I.; Moulis, C. Identification of the alkaloids of Galipea officinalis by gas chromatography-mass spectrometry. Phytochem. Anal. 2001, 12, 312-319.
13. Zhou, Y.-G. Asymmetric hydrogenation of heteroaromatic compounds. Acc. Chem. Res. 2007, 40, 1357-1366.
14. Tang, W.-J; Tan, J; Xu, L.-J; Lam, K.-H.; Fan, Q.-H.; Chan, A.S.C. Highly enantioselective hydrogenation of quinoline and pyridine derivatives with iridium-(P-Phos) catalyst. Adv. Synth. Catal. 2010, 352, 1055-1062.
15. Tang, W.; Sun, Y.; Xu, L.; Wang, T.; Fan, Q.; Lam, K.-H.; Chan, A.S.C. Highly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst. Org. Biomol. Chem. 2010, 8, 3464-3471.
16. Reetz, M.T.; Li, X. Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of BINOL-derived diphosphinites. Chem. Commun. 2006, 2159-2160.
17. Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Asymmetric hydrogenation of quinolines catalyzed by iridium with chiral ferrocenyloxazoline derived N,P ligands. Adv. Synth. Catal. 2004, 346, 909-912.
18. Lu, S.-M.; Bolm, C. Synthesis of sulfoximine-derived P,N ligands and their applications in asymmetric quinoline hydrogenations. Adv. Synth. Catal. 2008, 350, 1101-1105.
19. Eggenstein, M.; Thomas, A.; Theuerkauf, J.; Franciò, G.; Leitner, W. Highly efficient and versatile phosphine-phosphoramidite ligands for asymmetric hydrogenation. Adv. Synth. Catal. 2009, 351, 725-732.
20. Mršic, N.; Lefort, L.; Boogers, J.A.F.; Minnaard, A.J.; Feringa, B.L.; de Vries, J.G. Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of monodentate BINOL-derived phosphoramidites. Adv. Synth. Catal. 2008, 350, 1081-1089.
21. Lam, K.H.; Xu, L.; Feng, L.; Fan, Q.-H.; Lam, F.L.; Lo, W.-H.; Chan, A.S.C. Highly enantioselective iridium-catalyzed hydrogenation of quinoline derivatives using chiral phosphinite H8-BINAPO. Adv. Synth. Catal. 2005, 347, 1755-1758.
22. Suárez, A.; Méndez-Rojas, M.A.; Pizzano, A. Electronic differences between coordinating functionalities of chiral phosphine-phosphites and effects in catalytic enantioselective hydrogenation. Organometallics 2002, 21, 4611-4621.
23. Suárez, A.; Pizzano, A. New chiral phosphine-phosphites: a convenient synthesis based on the demethylation of o-anisyl phosphines and application in highly enantioselective catalytic hydrogenations. Tetrahedron: Asymm. 2001, 12, 2501-2504.
24. Rubio, M.; Suárez, A.; Álvarez, E.; Pizzano, A. Highly enantioselective hydrogenation of enol ester phosphonates catalyzed by rhodium phosphine-phosphite complexes. Chem. Commun. 2005, 628-630.
25. Rubio, M.; Vargas, S.; Suárez, A.; Álvarez, E.; Pizzano, A. Tuning of the structures of chiral phosphane-phosphites: application to the highly enantioselective synthesis of a-acyloxy phosphonates by catalytic hydrogenation. Chem. Eur. J. 2007, 13, 1821-1833.
26. Vargas, S.; Suárez, A.; Álvarez, E.; Pizzano, A. Highly enantioselective hydrogenation of enol ester phosphonates: a versatile procedure for the preparation of chiral β-hydroxyphosphonates. Chem. Eur. J. 2008, 14, 9856-9859.
27. Vargas, S.; Rubio, M.; Suárez, A.; del Río, D.; Álvarez, E.; Pizzano, A. Iridium complexes with phosphine-phosphite ligands. Structural aspects and application in the catalytic asymmetric hydrogenation of N-aryl imines. Organometallics 2006, 25, 961-973.
28. 3 symmetry. Chem. Commun. 1993, 3, 314-316.
29. Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. Highly enantioselective hydroformylation of olefins catalyzed by rhodium(I) complexes of new chiral phosphine-phosphite ligands. J. Am. Chem. Soc. 1997, 119, S4413-S4423.
30. Wang, D.-W.; Wang, X.-B.; Wang, D.-S.; Lu, S.-M.; Zhou, Y.-G.; Li, Y.-X. Highly enantioselective iridium-catalyzed hydrogenation of 2-belzylquinolines and 2-functionalyzed and 2,3-disubstituted quinolines. J. Org. Chem. 2009, 74, 2780-2787.
31. Akiyama, T. Stronger Brønsted acids. Chem. Rev. 2007, 107, 5744-5758.
32. Tadaoka, H.; Cartigny, D.; Nagano, T.; Gosavi, T.; Ayad, T.; Genêt, J.-P.; Ohshima, T.; Ratovelomanana-Vidal, V.; Mashima; K. Unprecedented halide dependence on catalytic asymmetric hydrogenation of 2-aryl and 2-alkyl-substituted quinolinium salts by using Ir complexes with Difluorphos and halide ligands. Chem. Eur. J. 2009, 15, 9990-9994.
33. Wang, D.-S.; Zhou, Y.-G. Asymmetric hydrogenation of quinolines activated by Brønsted acids. Tetrahrdron Lett. 2010, 51, 3014-3017.
34. Rueping, M.; Antonchick, A.P.; Theissmann, T.A Highly enantioselective Brønsted acid catalyzed Cascade reaction: organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids. Angew. Chem. Int. Ed. Engl. 2006, 45, 3683-3686.
35. Li, C.; Wang, C.; Villa-Marcos, B.; Xiao, J. Chiral counteranion-aided asymmetric hydrogenation of acyclic imines. J. Am. Chem. Soc. 2008, 130, 14450-14451.