Pd/NHC-catalyzed enantiospecific and regioselective suzuki-miyaura arylation of 2-arylaziridines: Synthesis of enantioenriched 2-arylphenethylamine derivatives

Journal of the American Chemical Society

Volumn 136, Issue 24, 2014, Pages 8544-8547

  Takeda, Youhei ^a   Ikeda, Yuki ^a   Kuroda, Akinobu ^a   Tanaka, Shino ^a   Minakata, Satoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS; ORGANIC COMPOUNDS; REGIOSELECTIVITY;

ARYLBORONIC ACIDS; CROSS-COUPLINGS; ENANTIOSPECIFIC; HYDRIDE ELIMINATION; N-HETEROCYCLIC CARBENE LIGANDS; PALLADIUM-CATALYZED; REGIO-SELECTIVE; STEREOGENIC CENTERS;

CATALYSIS;

AZIRIDINE DERIVATIVE; BORONIC ACID DERIVATIVE; LIGAND; PALLADIUM; PHENETHYLAMINE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DERIVATIZATION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 84902682680     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5039616     Document Type: Article

References (64)

1. Malinakova, H. C. Chem.-Eur. J. 2004, 10, 2636
2. Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656
3. Jarvo, E.; Taylor, B. Synlett 2011, 2761
4. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
5. Fischer, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 4594
6. Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 6694
7. Lou, S.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 1264
8. Lu, Z.; Wilsily, A.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 8154
9. Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180
10. Cordier, C. J.; Lundgren, R. J.; Fu, G. C. J. Am. Chem. Soc. 2013, 135, 10946
11. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129
12. Ye, J.; Bhatt, R. K.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 1
13. Li, L.; Wang, C.-Y.; Huang, R.; Biscoe, M. R. Nat. Chem. 2013, 5, 607
14. Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793
15. Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 63, 458
16. Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024
17. Sandrock, D. L.; Jean-Gérard, L.; Chen, C.-Y.; Dreher, S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 132, 17108
18. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191
19. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894
20. Hölzer, B.; Hoffmann, R. W. Chem. Commun. 2003, 732
21. Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-Y. J. Am. Chem. Soc. 2006, 128, 3538
22. Rodríguez, N.; Ramírez de Arellano, C.; Asensio, G.; Medio-Simón, M. Chem.-Eur. J. 2007, 13, 4223
23. López-Pérez, A.; Adrio, J.; Carretero, J. C. Org. Lett. 2009, 11, 5514
24. Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910
25. He, A.; Falck, J. R. J. Am. Chem. Soc. 2010, 132, 2524
26. Taylor, B. L. H.; Swift, E. C.; Waetzig, J. D.; Jarvo, E. R. J. Am. Chem. Soc. 2010, 133, 389
27. Greene, M. A.; Yonova, I. M.; Williams, F. J.; Jarvo, E. R. Org. Lett. 2012, 14, 4293
28. Taylor, B. L. H.; Harris, M. R.; Jarvo, E. R. Angew. Chem., Int. Ed. 2012, 51, 7790
29. Legros, J.-Y.; Toffano, M.; Fiaud, J.-C. Tetrahedron 1995, 51, 3235
30. Harris, M. R.; Hanna, L. E.; Greene, M. A.; Moore, C. E.; Jarvo, E. R. J. Am. Chem. Soc. 2013, 135, 3303
31. Zhou, Q.; Srinivas, H. D.; Dasgupta, S.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 3307
32. Maity, P.; Shacklady-McAtee, D. M.; Yap, G. P. A.; Sirianni, E. R.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 280
33. Li, M.-B.; Tang, X.-L.; Tian, S.-K. Adv. Synth. Catal. 2011, 353, 1980
34. Classics in Stereoselective Synthesis; Carreira, E. M.; Kvaerno, L., Eds.; Wiley-VCH: Weinheim, 2009.
35. Chiral Amine Synthesis; Methods, Developments and Applications; Nugent, T. C., Ed.; Wiley-VCH: Weinheim, 2010.
36. Zhang, A.; Neumeyer, J. L.; Baldessarini, R. J. Chem. Rev. 2007, 107, 274
37. Zhang, J.; Xiong, B.; Zhen, X.; Zhang, A. Med. Res. Rev. 2009, 29, 272
38. Michaelides, M. R.; Hong, Y.; DiDomenico, S., Jr.; Bayburt, E. K.; Asin, K. E.; Britton, D. R.; Lin, C. W.; Shiosaki, K. J. Med. Chem. 1997, 40, 1585
39. Farr, R. N.; Alabaster, R. J.; Chung, J. Y.; Craig, B.; Edwards, J. S.; Gibson, A. W.; Ho, G.-J.; Humphrey, G. R.; Johnson, S. A.; Grabowski, E. J. J. Tetrahedron: Asymmetry 2003, 14, 3503
40. Pineschi, M.; Bertolini, F.; Crotti, P.; Macchia, F. Org. Lett. 2006, 8, 2627
41. Kaiser, H. M.; Zenz, I.; Lo, W. F.; Spannenberg, A.; Schröder, K.; Jiao, H.; Gördes, D.; Beller, M.; Tse, M. K. J. Org. Chem. 2007, 72, 8847
42. Hajra, S.; Maji, B.; Mal, D. Adv. Synth. Catal. 2009, 351, 859
43. Yamashita, M.; Yamada, K.-I.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 1954
44. Wang, Z.-Q.; Feng, C.-G.; Zhang, S.-S.; Xu, M.-H.; Lin, G.-Q. Angew. Chem., Int. Ed. 2010, 49, 5780
45. Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006.
46. Lin, B. L.; Clough, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 2890
47. Ney, J. E.; Wolfe, J. P. J. Am. Chem. Soc. 2006, 128, 15415
48. Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2012, 134, 9541
49. Nielsen, D. K.; Huang, C.-Y.; Doyle, A. J. Am. Chem. Soc. 2013, 135, 13605
50. Alper, H.; Urso, F.; Smith, D. J. H. J. Am. Chem. Soc. 1983, 105, 6737
51. Calet, S.; Urso, F.; Alper, H. J. Am. Chem. Soc. 1989, 111, 931
52. Piotti, M. E.; Alper, H. J. Am. Chem. Soc. 1996, 118, 111
53. Baeg, J.-O.; Alper, H. J. Org. Chem. 1992, 57, 157
54. Baeg, J.-O.; Bensimon, C.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4700
55. Duda, M. L.; Michael, F. E. J. Am. Chem. Soc. 2013, 135, 18347
56. Wolfe, J. P.; Ney, J. E. Org. Lett. 2003, 5, 4607
57. Pd-catalyzed Aldol condensation of 4 to give 5 has been reported: Kim, J.-H.; Kulawiec, R. J. J. Org. Chem. 1996, 61, 7656
58. Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101
59. Panteleev, J.; Zhang, L.; Lautens, M. Angew. Chem., Int. Ed. 2011, 50, 9089
60. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787
61. Allylic alkoxylation pathway is also known for the activation of [(NHC)Pd(allyl)Cl] with a strong base (t -BuOK) in a polar solvent (DME): Viciu, M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470
62. Green, J. C.; Herbert, B. J.; Lonsdale, R. J. Organomet. Chem. 2005, 690, 6054
63. Stille, J. K. Oxidative Addition and Reductive Elimination. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R.; Patai, S., Eds.; John Wiley & Sons, Ltd.: New York, 1985; Vol. 2, p 625.
64. Chass, G. A.; O'Brien, C. J.; Hadei, N.; Kantchev, E. A. B.; Mu, W.-H.; Fang, D.-C.; Hopkinson, A. C.; Csizmadia, I. G.; Organ, M. G. Chem.-Eur. J. 2009, 15, 4281 Technology