Atroposelective Synthesis of Axially Chiral Biaryldiols via Organocatalytic Arylation of 2-Naphthols

Journal of the American Chemical Society

Volumn 137, Issue 48, 2015, Pages 15062-15065

  Chen, Ye Hui ^a   Cheng, Dao Juan ^a   Zhang, Jian ^a   Wang, Yong ^b   Liu, Xin Yuan ^a   Tan, Bin ^a  

^a SOUTHERN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

2-NAPHTHOLS; ASYMMETRIC TRANSFORMATIONS; CHIRAL COMPOUNDS; CHIRAL LIGAND; MILD REACTION CONDITIONS; ORGANOCATALYTIC; RAPID CONSTRUCTION; STEREOCONTROL;

PHOSPHORIC ACID;

2 NAPHTHOL; ALDEHYDE; DICHLOROMETHANE; DIETHYLZINC; PHOSPHORIC ACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINONE DERIVATIVE; SOLVENT; TOLUENE;

ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; ATROPOSELECTIVE SYNTHESIS; BROMINATION; CHIRALITY; CROSS COUPLING REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; ORGANOCATALYSIS; STEREOCHEMISTRY;

EID: 84949575631     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b10152     Document Type: Article

References (75)

1. Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155 10.1021/cr020025b
2. Brunel, J. M. Chem. Rev. 2005, 105, 857 10.1021/cr040079g
3. Brunel, J. M. Chem. Rev. 2007, 107, PR1 10.1021/cr078004a
4. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345 10.1021/ar00178a005
5. Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801 10.1021/cr040652w
6. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566 10.1002/anie.200353240
7. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356 10.1021/ja0491533
8. Akiyama, T. Chem. Rev. 2007, 107, 5744 10.1021/cr068374j
9. Terada, M. Chem. Commun. 2008, 4097 10.1039/b807577h
10. Rueping, M.; Kuenkel, A.; Atodiresei, I. Chem. Soc. Rev. 2011, 40, 4539 10.1039/c1cs15087a
11. Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047 10.1021/cr5001496
12. Kočovský, P.; Vyskočil, Š.; Smrčina, M. Chem. Rev. 2003, 103, 3213 10.1021/cr9900230
13. Ramon, D. J.; Yus, M. Chem. Rev. 2006, 106, 2126 10.1021/cr040698p
14. Shibasaki, M.; Matsunaga, S. Chem. Soc. Rev. 2006, 35, 269 10.1039/b506346a
15. Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384 10.1002/anie.200462661
16. Baudoin, O. Eur. J. Org. Chem. 2005, 2005, 4223 10.1002/ejoc.200500394
17. Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193 10.1039/b821092f
18. Tanaka, K. Chem.-Asian J. 2009, 4, 508 10.1002/asia.200800378
19. Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563 10.1021/cr100155e
20. Evans, D. A.; Dinsmore, C. J.; Watson, P. S.; Wood, M. R.; Richardson, T. I.; Trotter, B. W.; Katz, J. L. Angew. Chem., Int. Ed. 1998, 37, 2704 10.1002/(SICI)1521-3773(19981016)37:19<2704::AID-ANIE2704>3.0.CO;2-1
21. Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773 10.1021/ja016585u
22. Nicolaou, K. C.; Boddy, C. N. C. J. Am. Chem. Soc. 2002, 124, 10451 10.1021/ja020736r
23. Clayden, J.; Worrall, C. P.; Moran, W. J.; Helliwell, M. Angew. Chem., Int. Ed. 2008, 47, 3234 10.1002/anie.200705660
24. Burns, N. Z.; Krylova, I. N.; Hannoush, R. N.; Baran, P. S. J. Am. Chem. Soc. 2009, 131, 9172 10.1021/ja903745s
25. Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3, 1137 10.1021/ol015595x
26. Li, X.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500 10.1021/jo0340206
27. Yan, P.; Sugiyama, Y.; Takahashi, Y.; Kinemuchi, H.; Temma, T.; Habaue, S. Tetrahedron 2008, 64, 4325 10.1016/j.tet.2008.02.080
28. Egami, H.; Matsumoto, K.; Oguma, T.; Kunisu, T.; Katsuki, T. J. Am. Chem. Soc. 2010, 132, 13633 10.1021/ja105442m
29. Guo, F.; Konkol, L. C.; Thomson, R. J. J. Am. Chem. Soc. 2011, 133, 18 10.1021/ja108717r
30. Ma, G.; Sibi, M. P. Chem.-Eur. J. 2015, 21, 11644 10.1002/chem.201500869
31. Lu, S.; Poh, S. B.; Zhao, Y. Angew. Chem., Int. Ed. 2014, 53, 11041 10.1002/anie.201406192
32. Ma, G.; Deng, J.; Sibi, M. P. Angew. Chem., Int. Ed. 2014, 53, 11818 10.1002/anie.201406684
33. Mori, K.; Ichikawa, Y.; Kobayashi, M.; Shibata, Y.; Yamanaka, M.; Akiyama, T. J. Am. Chem. Soc. 2013, 135, 3964 10.1021/ja311902f
34. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668 10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z
35. Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383 10.1021/cr0306900
36. Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068 10.1002/anie.201006017
37. Zhuo, C. X.; Zhang, W.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 12662 10.1002/anie.201204822
38. Ryu, D. H.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 4800 10.1021/ja049323b
39. Aleman, J.; Richter, B.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5515 10.1002/anie.200701009
40. Aleman, J.; Cabrera, S.; Maerten, E.; Overgaard, J.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5520 10.1002/anie.200701207
41. Aleman, J.; Jacobsen, C. B.; Frisch, K.; Overgaard, J.; Jørgensen, K. A. Chem. Commun. 2008, 632 10.1039/B716485H
42. Wang, C.; Chen, X.-H.; Zhou, S.-M.; Gong, L.-Z. Chem. Commun. 2010, 46, 1275 10.1039/b917246g
43. Han, Z.-Y.; Chen, D.-F.; Wang, Y.-Y.; Guo, R.; Wang, P.-S.; Wang, C.; Gong, L.-Z. J. Am. Chem. Soc. 2012, 134, 6532 10.1021/ja3007148
44. Albrecht, L.; Gómez, C. V.; Jacobsen, C. B.; Jørgensen, K. A. Org. Lett. 2013, 15, 3010 10.1021/ol401204a
45. Hashimoto, T.; Nakatsu, H.; Takiguchi, Y.; Maruoka, K. J. Am. Chem. Soc. 2013, 135, 16010 10.1021/ja407501h
46. Liao, L.; Shu, C.; Zhang, M.; Liao, Y.; Hu, X.; Zhang, Y.; Wu, Z.; Yuan, W.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 10471 10.1002/anie.201405689
47. Zhang, Y.-C.; Zhao, J.-J.; Jiang, F.; Sun, S.-B.; Shi, F. Angew. Chem., Int. Ed. 2014, 53, 13912 10.1002/anie.201408551
48. Hashimoto, T.; Nakatsu, H.; Maruoka, K. Angew. Chem., Int. Ed. 2015, 54, 4617 10.1002/anie.201410957
49. Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2007, 46, 3951 10.1002/anie.200700064
50. Guo, Q.-X.; Wu, Z.-J.; Luo, Z.-B.; Liu, Q.-Z.; Ye, J.-L.; Luo, S.-W.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2007, 129, 13927 10.1021/ja074322f
51. Shen, X.; Jones, G. O.; Watson, D. A.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 11278 10.1021/ja104297g
52. Gustafson, J. L.; Lim, D.; Miller, S. J. Science 2010, 328, 1251 10.1126/science.1188403
53. Barrett, K. T.; Miller, S. J. J. Am. Chem. Soc. 2013, 135, 2963 10.1021/ja400082x
54. Li, G.-Q.; Gao, H.; Keene, G.; Devonas, M.; Ess, D. H.; Kürti, L. J. Am. Chem. Soc. 2013, 135, 7414 10.1021/ja401709k
55. De, C.; Pesciaioli, K. F.; List, B. Angew. Chem., Int. Ed. 2013, 52, 9293 10.1002/anie.201304039
56. Bhat, V.; Wang, S.; Stoltz, B. M.; Virgil, S. C. J. Am. Chem. Soc. 2013, 135, 16829 10.1021/ja409383f
57. Ros, A.; Estepa, B.; Ramírez-López, P.; álvarez, E.; Fernández, R.; Lassaletta, J. M. J. Am. Chem. Soc. 2013, 135, 15730 10.1021/ja4087819
58. Barrett, K. T.; Metrano, A. J.; Rablen, P. R.; Miller, S. J. Nature 2014, 509, 71 10.1038/nature13189
59. Zheng, J.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 13244 10.1002/anie.201408805
60. Link, A.; Sparr, C. Angew. Chem., Int. Ed. 2014, 53, 5458 10.1002/anie.201402441
61. Armstrong, R. J.; Smith, M. D. Angew. Chem., Int. Ed. 2014, 53, 12822 10.1002/anie.201408205
62. Hazra, C. K.; Dherbassy, Q.; Wencel-Delord, J.; Colobert, F. Angew. Chem., Int. Ed. 2014, 53, 13871 10.1002/anie.201407865
63. Meyers, A. I.; Wettlaufer, D. G. J. Am. Chem. Soc. 1984, 106, 1135 10.1021/ja00316a063
64. Nishii, Y.; Wakasugi, K.; Koga, K.; Tanabe, Y. J. Am. Chem. Soc. 2004, 126, 5358 10.1021/ja0319442
65. De, C. K.; Pesciaioli, F.; List, B. Angew. Chem., Int. Ed. 2013, 52, 9293 10.1002/anie.201304039
66. Li, G.-Q.; Gao, H.; Keene, C.; Devonas, M.; Ess, D. H.; Kurti, L. J. Am. Chem. Soc. 2013, 135, 7414 10.1021/ja401709k
67. Cheng, D.-J.; Yan, L.; Tian, S.-K.; Wu, M.-Y.; Wang, L.-X.; Fan, Z.-L.; Zheng, S.-C.; Liu, X.-Y.; Tan, B. Angew. Chem., Int. Ed. 2014, 53, 3684 10.1002/anie.201310562
68. Fang, Z.-J.; Zheng, S.-C.; Guo, Z.; Guo, J.-Y.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2015, 54, 9528 10.1002/anie.201503207
69. Yu, P.; Lin, J.-S.; Li, L.; Zheng, S.-C.; Xiong, Y.-P.; Zhao, L.-J.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2014, 53, 11890 10.1002/anie.201405401
70. Lin, J.-S.; Yu, P.; Huang, L.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2015, 54, 7847 10.1002/anie.201501762
71. For the first use of this substrate in an asymmetric reaction, see: Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162 10.1021/ja0367602
72. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457 10.1021/cr00039a007
73. Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757 10.1021/cr000411y
74. Zhang, F.-Y.; Yip, C.-W.; Cao, R.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 585 10.1016/S0957-4166(97)00024-4
75. Mori, M.; Nakai, T. Tetrahedron Lett. 1997, 38, 6233 10.1016/S0040-4039(97)01433-0