Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids

Journal of the American Chemical Society

Volumn 135, Issue 38, 2013, Pages 14044-14047

  Neel, Andrew J ^a   Hehn, Jörg P ^a   Tripet, Pascal F ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOND-FORMING REACTIONS; CHIRAL PHOSPHATE ANIONS; CYCLIC AMINALS; DESIGN AND APPLICATION; ENANTIOSELECTIVE; HYDROGEN BONDING INTERACTIONS; STERIC BULK;

HYDROGEN BONDS; PHOSPHORIC ACID;

ENANTIOSELECTIVITY;

2,2' DIHYDROXY 1,1' BINAPHTHYL; PHOSPHORIC ACID; TETRAHYDROISOQUINOLINE; TRIAZOLE;

AMIDATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL INTERACTION; CHIRALITY; CLICK CHEMISTRY; CROSS COUPLING REACTION; CYCLOADDITION; DEHYDROGENATION; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; NUCLEOPHILICITY;

CATALYSIS; DRUG DESIGN; HYDROGEN BONDING; PHOSPHORIC ACIDS; STEREOISOMERISM; TETRAHYDROISOQUINOLINES; TRIAZOLES;

EID: 84884893454     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja407410b     Document Type: Article

References (72)

1. Phipps, R. J.; Hamilton, G. L.; Toste, F. D. Nature Chem. 2012, 4, 603
2. Mahlau, M.; List, B. Angew Chem., Int. Ed. 2013, 52, 518
3. Brak, K.; Jacobsen, E. N. Angew Chem., Int. Ed. 2013, 52, 534
4. Terada, M. Curr. Org. Chem. 2011, 15, 2227
5. Terada, M. Synthesis 2010, 12, 1929
6. Akiyama, T. Chem. Rev. 2007, 107, 5744
7. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496
8. Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336
9. Rueping, M.; Antonchick, A.; Brinkmann, C. Angew. Chem., Int. Ed. 2007, 46, 6903
10. Liao, S.; List, B. J. Am. Chem. Soc. 2010, 49, 628
11. Jiang, G.; Halder, R.; Fang, Y.; List, B. Angew. Chem., Int. Ed. 2011, 50, 9752
12. Rauniyar, V.; Wang, Z.; Burks, H.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 8486
13. Chai, Z.; Rainey, T. J. Am. Chem. Soc. 2012, 134, 3615
14. Zbieg, J.; Yamaguchi, E.; McInturff, E.; Krische, M. Science 2012, 336, 324
15. Ohmatsu, K.; Ito, M.; Kunieda, T.; Ooi, T. Nature Chem. 2012, 4, 473
16. Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193
17. Wang, X.; List, B. Angew. Chem., Int. Ed. 2008, 47, 1119
18. Hamilton, G. L.; Kanai, T.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 14984
19. Rueping, M.; Uria, U.; Lin, M.-Y.; Atodiresei, I. J. Am. Chem. Soc. 2011, 133, 3732
20. For a discussion of H-bonding/ion-pair continuum, see: Fleischmann, M.; Drettwan, D.; Sugiono, E.; Rueping, M.; Gschwind, R. Angew. Chem., Int. Ed. 2011, 50, 6364
21. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
22. Scheuerrmann, C. J. Chem. Asian J. 2010, 5, 436
23. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
24. Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997
25. Guo, C.; Song, J.; Gong, L.-Z. Angew. Chem., Int. Ed. 2010, 49, 5558
26. Zhang, G.; Zhang, Y.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 10429
27. Zhang, J.; Tiwari, B.; Xing, C.; Chen, X.; Chi, Y. Angew. Chem., Int. Ed. 2012, 51, 3649
28. Zhang, G.; Ma, Y.; Wang, S.; Zhang, Y.; Wang, R. J. Am. Chem. Soc. 2012, 134, 12334
29. Zhang, G.; Ma, Y.; Wang, S.; Kong, W.; Wang, R. Chem. Sci. 2013, 4, 2645
30. Cui, Y.; Villafane, L.; Clausen, D.; Floreancig, P. Tetrahedron 2013, 69, 7618
31. Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317
32. Rauniyar, V.; Lackner, A. D.; Hamilton, G. L.; Toste, F. D. Science 2011, 334, 1681
33. Phipps, R.; Hiramatsu, K.; Toste, F. D. J. Am. Chem. Soc. 2012, 134, 8376
34. Wang, Y.-M.; Wu, J.; Hoong, C.; Rauniyar, V.; Toste, F. D. J. Am. Chem. Soc. 2012, 134, 12928
35. Phipps, R.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 1268
36. Shunatona, H. P.; Fruh, N.; Wang, Y.-M.; Rauniyar, V.; Toste, F. D. Angew. Chem., Int. Ed. 2013, 52, 7724
37. Wu, J.; Wang, Y.-M.; Drljevic, A.; Rauniyar, V.; Phipps, R. J.; Toste, F. D. Proc. Natl. Acad. Sci. 2013, 110, 13729
38. Bobbit, J.; Brückner, C.; Merbouh, N. Org. React. 2010, 74, 103
39. Mancheño, O.; Stopka, T. Synthesis 2013, 45, 1602
40. Richter, H.; Mancheño, O. Eur. J. Org. Chem. 2010, 4460
41. Richter, H.; Mancheño, O. Org. Lett. 2011, 13, 6066
42. Wertz, S.; Kodama, S.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 11511
43. Simón, L.; Goodman, J. J. Org. Chem. 2011, 76, 1775
44. Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804
45. Cheng, X.; Vellalath, S.; Goddard, R.; List, B. J. Am. Chem. Soc. 2008, 130, 15786
46. Bachu, P.; Akiyama, T. Chem. Commun. 2010, 46, 4112
47. Shapiro, N. D.; Rauniyar, V.; Hamilton, G. L.; Wu, J.; Toste, F. D. Nature 2011, 470, 245
48. Čorić, I.; List, B. Nature 2012, 483, 315
49. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
50. Knowles, R. R.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030
51. Knowles, R. R.; Jacobsen, E. N. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20678
52. Beckendorf, S.; Mancheño, O. G. Synthesis 2012, 44, 2162
53. Recsei, C.; McErlean, S. P. Tetrahedron 2012, 68, 464
54. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
55. Tornøe, C.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057
56. Rostovtsev, V.; Green, L.; Fokin, V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
57. Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302
58. Hua, Y.; Flood, A. Chem. Soc. Rev. 2010, 39, 1262
59. Juríček, M.; Kouwer, P. H.; Rowan, A. Chem. Commun. 2011, 47, 8740
60. Kumar, A.; Pandey, P. Org. Lett. 2008, 10, 165
61. Leigh, D.; Robertson, C.; Slawin, A.; Thompson, P. J. Am. Chem. Soc. 2013, 135, 9939
62. Beckendorf, S.; Asmus, S.; Mück-Lichtenfeld, C.; Mancheño, O. G. Chem.-Eur. J. 2013, 19, 1581
63. Valverde, I.; Mindt, T. Chimia 2013, 67, 262
64. Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905
65. Kolb, H. C.; Sharpless, K. B. Drug Discov. Today 2003, 8, 1128
66. Brik, A.; Alexandratos, J.; Lin, Y.-C.; Elder, J.; Olson, A. J.; Wlodawer, A.; Goodsell, D. S.; Wong ChemBioChem 2005, 6, 1167
67. Escorihuela, J.; Burguete, M. I.; Luis, S. V. Chem. Soc. Rev. 2013, 42, 5595
68. Bartók, M. Chem. Rev. 2010, 110, 1663
69. Li, N.; Chen, X.-H.; Song, J.; Luo, S.-W.; Fan, W.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 15301
70. Jiang, J.; Xu, H.-D.; Xi, J.-B.; Ren, B.-Y.; Lv, F.-P.; Guo, X.; Jiang, L.-Q.; Zhang, Z.-Y.; Hu, W.-H. J. Am. Chem. Soc. 2011, 133, 8428
71. Rueping, M.; Antonchick, A. P.; Sugiono, E.; Grenader, K. Angew. Chem., Int. Ed. 2009, 48, 908 and ref 13b
72. Honjo, T.; Phipps, R. J.; Rauniyar, V.; Toste, F. D. Angew. Chem., Int. Ed. 2012, 51, 9684