Chiral molecular tweezers: Synthesis and reactivity in asymmetric hydrogenation

Journal of the American Chemical Society

Volumn 137, Issue 12, 2015, Pages 4038-4041

  Lindqvist, Markus ^a   Borre, Katja ^a   Axenov, Kirill ^a   Kótai, Bianka ^b   Nieger, Martin ^a   Leskelä, Markku ^a   Pápai, Imre ^b   Repo, Timo ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

AMINOBORANES; ASYMMETRIC HYDROGENATION; CATALYTIC CYCLES; ENAMINES; HYDRIDE TRANSFERS; MOLECULAR TWEEZERS; NON-COVALENT; REACTION MECHANISM;

HYDROGENATION;

AMINOBORANE; BORANE DERIVATIVE; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; HYDROGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84926367156     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja512658m     Document Type: Article

References (61)

1. Spindler, F.; Blaser, H.-U. Enantioselective Hydrogenation of C=N Functions and Enamines. In Handbook of Homogenous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; Vol. 3, pp 1193-1214.
2. Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713
3. Yu, Z.; Jin, W.; Jiang, Q. Angew. Chem., Int. Ed. 2012, 51, 6060
4. Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Soc. Rev. 2012, 41, 4126
5. Nugent, T. C. Chiral Amine Synthesis: Methods, Developments and Applications; Wiley-VCH: Weinheim, Germany, 2010.
6. Nugent, T. C.; El-Shazly, M. Adv. Synth Catal. 2010, 352, 753
7. Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889
8. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726
9. Welch, G. C.; San Juan, R. R.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124
10. Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535
11. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 171
12. Powers, P. P. Nature 2010, 463, 171
13. Erker, G. C. R. Chim. 2011, 14, 831
14. Stephan, D. W. Org. Biomol. Chem. 2012, 10, 5740
15. Hounjet, L. J.; Stephan, D. W. Org. Process Res. Dev. 2014, 18, 385
16. Paradies, J. Angew. Chem., Int. Ed. 2014, 53, 3552
17. Feng, X.; Du, H. Tetrahedron Lett. 2014, 55, 6959
18. Shi, L.; Zhou, Y.-G. ChemCatChem 2015, 7, 54
19. Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 8050
20. Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Fröhlich, R.; Erker, G. Angew. Chem., Int. Ed. 2008, 47, 7543
21. Chase, P. A.; Jurca, T.; Stephan, D. W. Chem. Commun. 2008, 1701
22. Sumerin, V.; Schulz, F.; Atsumi, M.; Wang, C.; Nieger, M.; Leskelä, M.; Repo, T.; Pyykkö, P.; Rieger, B. J. Am. Chem. Soc. 2008, 130, 14117
23. Jiang, C.; Blacque, O.; Berke, H. Chem. Commun. 2009, 5518
24. Rokob, T. A.; Hamza, A.; Stirling, A.; Pápai, I. J. Am. Chem. Soc. 2009, 131, 2029
25. Axenov, K. V.; Kehr, G.; Frölich, R.; Erker, G. J. Am. Chem. Soc. 2009, 131, 3454
26. Axenov, K. V.; Kehr, G.; Frölich, R.; Erker, G. Organometallics 2009, 28, 5148
27. Eros, G.; Mehdi, H.; Pápai, I.; Rokob, T. A.; Király, P.; Tárkányi, G.; Soós, T. Angew. Chem., Int. Ed. 2010, 49, 6559
28. Farrell, J. M.; Hatnean, J. A.; Stephan, D. W. J. Am. Chem. Soc. 2012, 134, 15728
29. Chernichenko, K.; Nieger, M.; Leskelä, M.; Repo, T. Dalton Trans. 2012, 41, 9029
30. Wang, G.; Chen, C.; Du, T.; Zhong, W. Adv. Synth. Catal. 2014, 356, 1747
31. Hatnean, J. A.; Thomson, J. W.; Chase, P. A.; Stephan, D. W. Chem. Commun. 2014, 50, 301
32. Geier, S. J.; Chase, P. A.; Stephan, D. W. Chem. Commun. 2010, 46, 4884
33. Stephan, D. W.; Greenberg, S.; Graham, T. W.; Chase, P.; Hastie, J. J.; Geier, S. J.; Farrell, J. M.; Brown, C. C.; Heiden, Z. M.; Welch, G. C.; Ullrich, M. Inorg. Chem. 2011, 50, 12338
34. Eros, G.; Nagy, K.; Pápai, I.; Nagy, P.; Király, G.; Tárkányi, G.; Soós, T. Chem.-Eur. J. 2012, 18, 574
35. Scott, D. J.; Fuchter, M. J.; Ashley, A. E. Angew. Chem., Int. Ed. 2014, 53, 10218
36. Clark, E. R.; Ingleson, M. J. Angew. Chem., Int. Ed. 2014, 53, 11306
37. Mahdi, T.; Stephan, D. W. J. Am. Chem. Soc. 2014, 136, 15809
38. Scott, D. J.; Fuchter, M. J.; Ashley, A. E. J. Am. Chem. Soc. 2014, 136, 15813
39. Chen, D.; Klankermayer, J. Chem. Commun. 2008, 2130
40. Chen, D.; Wang, Y.; Klankermayer, J. Angew. Chem., Int. Ed. 2010, 49, 9475
41. Ghattas, G.; Chen, D.; Pan, F.; Klankermayer, J. Dalton Trans. 2012, 41, 9026
42. Liu, Y.; Du, H. J. Am. Chem. Soc. 2013, 135, 6810
43. Wei, S.; Du, H. J. Am. Chem. Soc. 2014, 136, 12261
44. Zhang, Z.; Du, H. Angew. Chem., Int. Ed. 2015, 54, 623
45. Rokob, T. A.; Hamza, A.; Pápai, I. J. Am. Chem. Soc. 2009, 131, 10701
46. Rokob, T. A.; Pápai, I. Top. Curr. Chem. 2013, 332, 157
47. Sumerin, V.; Chernichenko, K.; Nieger, M.; Leskelä, M.; Rieger, B.; Repo, T. Adv. Synth. Catal. 2011, 353, 2093
48. Singaram, B.; Goralski, C. T.; Rangaishenvi, M. V.; Brown, H. C. J. Am. Chem. Soc. 1989, 111, 384
49. Sigaram, B.; Rangaishenvi, M. V.; Brown, H. C.; Goralski, C. T.; Hasha, D. L. J. Org. Chem. 1991, 56, 1543
50. Singaram, B.; Goralski, C. T.; Fisher, G. B. J. Org. Chem. 1991, 56, 5691
51. Parks, D. J.; Piers, W. E.; Yap, G. P. A. Organometallics 1998, 17, 5492
52. Schwendemann, S.; Oishi, S.; Saito, S.; Fröhlich, R.; Kehr, G.; Erker, G. Chem.-Asian J. 2013, 8, 212
53. Lindqvist, M.; Axenov, K.; Nieger, M.; Räisänen, M.; Leskelä, M.; Repo, T. Chem.-Eur. J. 2013, 19, 10412
54. Morrison, D. J.; Piers, W. E.; Parvez, M. Synlett 2004, 2429
55. García-Fortanet, J.; Kessler, F.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 6676
56. Juríček, M.; Brath, H.; Kasák, P.; Putala, M. J. Organomet. Chem. 2007, 692, 5279
57. Brath, H.; Mešková, M.; Putala, M. Eur. J. Org. Chem. 2009, 3315
58. Mešková, M.; Putala, M. Tetrahedron Lett. 2011, 52, 5379
59. Jeulin, S.; de Paule, S. D.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799
60. Schwendemann, S.; Tumay, T. A.; Axenov, K. V.; Peuser, I.; Kehr, G.; Fröhlich, R.; Erker, G. Organometallics 2010, 29, 1067
61. Stephan, D. W.; Erker, G. Top. Curr. Chem. 2013, 332, 85