Relay iron/chiral brønsted acid catalysis: Enantioselective hydrogenation of benzoxazinones

Journal of the American Chemical Society

Volumn 137, Issue 7, 2015, Pages 2763-2768

  Lu, Liang Qiu ^a,b   Li, Yuehui ^b   Junge, Kathrin ^b   Beller, Matthias ^b  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; ENANTIOSELECTIVITY; LIGANDS; PHOSPHORUS COMPOUNDS;

ACID CATALYSIS; ASYMMETRIC HYDROGENATION; BENZOXAZINONES; ENANTIOSELECTIVE HYDROGENATION; ENANTIOSELECTIVE REDUCTION; HIGH YIELD; PHOSPHINE LIGANDS;

HYDROGENATION;

BENZOXAZINONE DERIVATIVE; BRONSTED ACID; HETEROCYCLIC COMPOUND; IRON; LIGAND; PHOSPHINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; REACTION TIME; SYNTHESIS;

EID: 84923556954     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b00085     Document Type: Article

References (57)

1. Knowles, W. S. Angew. Chem., Int. Ed. 2002, 41, 1998
2. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008
3. Blaser, H.-U. Industrial Asymmetric Hydrogenation. In Applications of Transition Metal Catalysis in Drug Discovery and Development: An Industrial Perspective; Crawley, M. L.; Trost, B. M., Eds.; John Wiley & Sons: Hoboken, NJ, 2008.
4. Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557
5. A selected review on Pd-catalyzed AH reactions: Chen, Q.-A.; Ye, Z.-S.; Duan, Y.; Zhou, Y.-G. Chem. Soc. Rev. 2013, 42, 497
6. Monfette, S.; Turner, Z. R.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2012, 134, 4561
7. Friedfeld, M. R.; Shevlin, M.; Hoyt, J.; Krska, S. W.; Tudge, M.; Chirik, P. J. Science 2013, 342, 1076
8. Hamada, Y.; Koseki, Y.; Fujii, T.; Maeda, T.; Hibino, T.; Makino, K. Chem. Commun. 2008, 6206
9. Hibino, T.; Makino, K.; Sugiyama, T.; Hamada, Y. ChemCatChem 2009, 1, 237
10. Shimizu, H.; Igarashi, D.; Kuriyama, W.; Yusa, Y.; Sayo, N.; Saito, T. Org. Lett. 2007, 9, 1655
11. Junge, K.; Wendt, B.; Addis, D.; Zhou, S.; Das, S.; Fleischer, S.; Beller, M. Chem.-Eur. J. 2010, 17, 101
12. Werkmeister, S.; Fleischer, S.; Junge, K.; Beller, M. Chem.-Asian J. 2012, 7, 2562
13. Zuo, W.; Tauer, S.; Prokopchuk, D. E.; Morris, R. H. Organometallics 2014, 33, 5791
14. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317
15. Plietker, B. Iron Catalysis in Organic Chemistry; Wiley-VCH: Weinheim, 2008.
16. Plietker, B. Iron Catalysis. Topics in Organometallic Chemistry; Springer: Heidelberg, 2011; Vol. 33.
17. Nakazawa, H.; Itazaki, M. Top. Organomet. Chem. 2011, 33, 27
18. Junge, K.; Schröder, K.; Beller, M. Chem. Commun. 2011, 47, 4849
19. Darwish, M.; Wills, M. Catal. Sci. Technol. 2012, 2, 243
20. Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. H. Angew. Chem., Int. Ed. 2008, 47, 940
21. Berkessel, A.; Reichau, S.; Von der Höh, A.; Leconte, N.; Nordörfl, J.-M. Organometallics 2011, 30, 3880
22. Berkessel, A.; Van der Höh, A. ChemCatChem 2011, 3, 861
23. Lagaditis, P. O.; Sues, P. E.; Sonnenberg, J. F.; Wan, K. Y.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2014, 136, 1367
24. Li, Y.; Yu, S.; Wu, X.; Xiao, J.; Shen, W.; Dong, Z.; Gao, J. J. Am. Chem. Soc. 2014, 136, 4031
25. Zhou, S.; Fleischer, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 5120
26. Fleischer, S.; Werkmeister, S.; Zhou, S.; Junge, K.; Beller, M. Chem.-Eur. J. 2012, 18, 9005
27. Fleischer, S.; Zhou, S.; Werkmeister, S.; Junge, K.; Beller, M. Chem.-Eur. J. 2013, 19, 4997
28. Ilaš, J.; Anderluh, P. Š.; Dolenc, M. S.; Kikelj, D. Tetrahedron 2005, 61, 7325
29. Macías, F. A.; Marín, D.; Oliveros-Bastidasab, A.; Molinillo, J. M. G. Nat. Prod. Rep. 2009, 26, 478
30. Osbourn, A. E.; Lanzotti, V. Plant-Derived Natural Products: Synthesis, Function, and Application; Springer: Heidelberg, 2009.
31. Gorohovsky, S.; Bittner, S. Amino Acids 2001, 20, 135
32. Wolfer, J.; Bekele, T.; Abraham, C. J.; Dogo-Isonagie, C.; Lectka, T. Angew. Chem., Int. Ed. 2006, 45, 7398
33. Paull, D. H.; Alden-Danforth, E.; Wolfer, J.; Dogo-Isonagie, C.; Abraham, C. J.; Lectka, T. J. Org. Chem. 2007, 72, 5380
34. Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 6751
35. Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84
36. Malkov, A. V.; Vranková, K.; Stončius, S.; Kočovský, P. J. Org. Chem. 2009, 74, 5839
37. Xue, Z.-Y.; Jiang, Y.; Peng, X.-Z.; Yuan, W.-C.; Zhang, X.-M. Adv. Synth. Catal. 2010, 352, 2132
38. Xue, Z.-Y.; Jiang, Y.; Yuan, W. C.; Zhang, X. M. Eur. J. Org. Chem. 2010, 616
39. Chen, Q.-A.; Chen, M.-W.; Yu, C.-B.; Shi, L.; Wang, D.-S.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2011, 133, 16432
40. Chen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2012, 134, 2442
41. Núñez-Rico, J. L.; Vidal-Ferran, A. Org. Lett. 2013, 15, 2066
42. Ouellet, S. G.; Walji, A. M.; MacMillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327
43. Connon, S. J. Org. Biomol. Chem. 2007, 5, 3407-3417
44. Rueping, M.; Dufour, J.; Schoepke, F. R. Green Chem. 2011, 13, 1084
45. Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498-2518
46. Du, W.; Yu, Z. Synlett 2012, 1300
47. Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem.-Eur. J. 2010, 16, 9350
48. Shi, F.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 11423
49. Han, Z.-Y.; Wang, C.; Gong, L.-Z. In Science of Synthesis, Asymmetric Organocatalysis; Maruoka, K., Ed.; Georg ThiemeVerlag: Stuttgart, 2012; Vol. 2, p 697.
50. Chen, J.-R.; Hu, X.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2014, 53, 4038
51. Cai, Q.; Zhao, Z.-A.; You, S.-L. Angew. Chem., Int. Ed. 2009, 48, 7428
52. Cai, Q.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 8666
53. An, X.-L.; Chen, J.-R.; Li, C.-F.; Zhang, F.-G.; Zou, Y.-Q.; Guo, Y.-C.; Xiao, W.-J. Chem.-Asian J. 2010, 5, 2258
54. Yang, Z.-P.; Zhang, W.; You, S.-L. J. Org. Chem. 2014, 79, 7785
55. Quintard, A.; Constantieux, T.; Rodriguez, J. Angew. Chem., Int. Ed. 2013, 52, 12883
56. Lu, L.-Q.; Li, Y.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 8382
57. Fe3(CO)12 was found a good catalyst to promote the hydrogenation of imine units, see: Fleischer, S.; Zhou, S.; Junge, K.; Beller, M. Chem.-Asian J. 2011, 6, 2240