Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling

Organic Letters

Volumn 17, Issue 4, 2015, Pages 940-943

  Hoang, Gia L ^a   Yang, Zhao Di ^a,b   Smith, Sean M ^a   Pal, Rhitankar ^c   Miska, Judy L ^a   Pérez, Damaris E ^a   Pelter, Libbie S W ^d   Zeng, Xiao Cheng ^a   Takacs, James M ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

^b HARBIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c YALE UNIVERSITY   (United States)

^d PURDUE UNIVERSITY CALUMET   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BORON DERIVATIVE; CROSS LINKING REAGENT; PALLADIUM; RHODIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

AMIDES; BORON COMPOUNDS; CATALYSIS; CROSS-LINKING REAGENTS; MOLECULAR STRUCTURE; PALLADIUM; RHODIUM; STEREOISOMERISM;

EID: 84923339093     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503764d     Document Type: Article

References (56)

1. Li, L.; Zhao, S.; Joshi-Pangu, A.; Diane, M.; Biscoe, M. R. J. Am. Chem. Soc. 2014, 136, 14027-14030
2. Matthew, S. C.; Glasspoole, B. W.; Eisenberger, P.; Crudden, C. M. J. Am. Chem. Soc. 2014, 136, 5828-5831
3. Buesking, A. W.; Ellman, J. A. Chem. Sci. 2014, 5, 1983-1987
4. Bonet, A.; Odachowski, M.; Leonori, D.; Essafi, S.; Aggarwal, V. K. Nat. Chem. 2014, 6, 584-589
5. Zhang, C.; Yun, J. Org. Lett. 2013, 15, 3416-3419
6. Mlynarski, S. N.; Karns, A. S.; Morken, J. P. J. Am. Chem. Soc. 2012, 134, 16449-16451
7. Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024-2025
8. Leonori, D.; Aggarwal, V. K. Angew. Chem.; Int. Ed. 2015, 54, 1082-1096
9. Swift, E. C.; Jarvo, E. R. Tetrahedron 2013, 69, 5799-5817
10. Stoichiometric reagents: Brown, J. M.; Nguyen, B. N. Stereoselective hydroboration and diboration of carbon-carbon double bonds; Georg Thieme Verlag: 2011; Vol. 1, pp 295-324.
11. Mlynarski, S. N.; Schuster, C. H.; Morken, J. P. Nature 2014, 505, 386-90
12. Sun, C.; Potter, B.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 6534-6537
13. Dewhurst, R. D.; Marder, T. B. Nat. Chem. 2014, 6, 279-280
14. Enantioselective B-H bond insertion: Cheng, Q.; Zhu, S.; Zhang, Y.; Xie, X.; Zhou, Q. J. Am. Chem. Soc. 2013, 135, 14094-14097
15. Radomkit, S.; Hoveyda, A. H. Angew. Chem.; Int. Ed. 2014, 53, 3387-3391
16. Luo, Y.; Roy, I. D.; Madec, A. G. E.; Lam, H. W. Angew. Chem.; Int. Ed. 2014, 53, 4186-4190
17. Calow, A. D. J.; Batsanov, A. S.; Pujol, A.; Sole, C.; Fernandez, E.; Whiting, A. Org. Lett. 2013, 15, 4810-4813
18. Callow, A. D. J.; Whiting, A. Org. Biomol. Chem. 2012, 10, 5485-5497
19. Verendel, J. J.; Pamies, O.; Dieguez, M.; Andersson, P. G. Chem. Rev. 2014, 114, 2130-2169
20. Boese, D.; Niesobski, P.; Luebcke, M.; Pietruszka, J. J. Org. Chem. 2014, 79, 4699-4703
21. Lee, J. C. H.; Hall, D. G. J. Am. Chem. Soc. 2010, 132, 5544-5545
22. Yu, Z.; Ely, R. J.; Morken, J. P. Angew. Chem.; Int. Ed. 2014, 53, 9632-9636
23. Coombs, J. R.; Haeffner, F.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 11222-11231
24. Ferris, G. E.; Hong, K.; Roundtree, I. A.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 2501-2504
25. Kliman, L. T.; Mlynarski, S. N.; Ferris, G. E.; Morken, J. P. Angew. Chem.; Int. Ed. 2012, 51, 521-524
26. Schuster, C. H.; Li, B.; Morken, J. P. Angew. Chem.; Int. Ed. 2011, 50, 7906-7909
27. Burks, H. E.; Morken, J. P. Chem. Commun. 2007, 4717-4725
28. Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2013, 135, 4934-4937
29. Hong, K.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 9252-9254
30. He, Z.; Zhao, Y.; Tian, P.; Wang, C.; Dong, H.; Lin, G. Org. Lett. 2014, 16, 1426-1429
31. Feng, X.; Jeon, H.; Yun, J. Angew. Chem.; Int. Ed. 2013, 52, 3989-3992
32. Kubota, K.; Yamamoto, E.; Ito, H. Adv. Synth. Catal. 2013, 355, 3527-3531
33. Moteki, S. A.; Toyama, K.; Liu, Z.; Ma, J.; Holmes, A. E.; Takacs, J. M. Chem. Commun. 2012, 48, 263-265
34. Sasaki, Y.; Zhong, C.; Sawamura, M.; Ito, H. J. Am. Chem. Soc. 2010, 132, 1226-1227
35. Carroll, A.; O'Sullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609-631
36. Smith, S. M.; Hoang, G. L.; Pal, R.; Khaled, M. O. B.; Pelter, L. S. W.; Zeng, X. C.; Takacs, J. M. Chem. Commun. 2012, 48, 12180-12182
37. Smith, S. M.; Uteuliyev, M.; Takacs, J. M. Chem. Commun. 2011, 47, 7812-7814
38. Smith, S. M.; Takacs, J. M. J. Am. Chem. Soc. 2010, 132, 1740-1741
39. Smith, S. M.; Takacs, J. M. Org. Lett. 2010, 12, 4612-4615
40. Smith, S. M.; Thacker, N. C.; Takacs, J. M. J. Am. Chem. Soc. 2008, 130, 3734-3735
41. For a related computational study, see: Yang, Z.; Pal, R.; Hoang, G. L.; Zeng, X. C.; Takacs, J. M. ACS Catal. 2014, 4, 763-773
42. Fernandez-Perez, H.; Etayo, P.; Lao, J. R.; Nunez-Rico, J.; Vidal-Ferran, A. Chem. Commun. 2013, 49, 10666-10675
43. Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198-7199
44. Perez Luna, A.; Bonin, M.; Micouin, L.; Husson, H. J. Am. Chem. Soc. 2002, 124, 12098-12099
45. Brunel, J.; Buono, G. Tetrahedron Lett. 1999, 40, 3561-3564
46. Burgess, K.; Ohlmeyer, M. J. J. Org. Chem. 1988, 53, 5178-9
47. Escorihuela, J.; Burguete, M. I.; Luis, S. V. Chem. Soc. Rev. 2013, 42, 5595-1617
48. Lennox, A. J. J.; Lloyd-Jones, G. Angew. Chem.; Int. Ed. 2012, 51, 9385-9388
49. Molander, G. A.; Shin, I.; Jean-Gerard, L. Org. Lett. 2010, 12, 4384-4387
50. Molander, G. A.; Wisniewski, S. R. J. Am. Chem. Soc. 2012, 134, 16856-16868
51. Bruno, N. C.; Tudge, M. T.; Buchwald, S. L. Chem. Sci. 2013, 4, 916-920
52. Sandrock, D. L.; Jean-Gerard, L.; Chen, C.; Dreher, S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 132, 17108-17110
53. Awano, T.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 20738-20741
54. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191-13193
55. Lee, J. C.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894-899
56. Lennox, A. J. J.; Lloyd-Jones, G. Chem. Soc. Rev. 2014, 43, 412-443