Catalytic asymmetric insertion of diazoesters into Aryl-CHO bonds: Highly enantioselective construction of chiral all-carbon quaternary centers

Journal of the American Chemical Society

Volumn 135, Issue 39, 2013, Pages 14556-14559

  Gao, Lizhu ^a   Kang, Byung Chul ^a   Ryu, Do Hyun ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; ENANTIOSELECTIVE; ENANTIOSELECTIVE CONSTRUCTION; FUNCTIONALIZED; QUATERNARY CENTERS;

CARBON;

ENANTIOSELECTIVITY;

BORON; ESTER;

AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHIRALITY; CYCLOPROPANATION; ENANTIOSELECTIVITY; NUCLEOPHILICITY; ORGANIC CHEMISTRY; STEREOCHEMISTRY;

EID: 84885149894     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja408196g     Document Type: Article

References (67)

1. Buchner, K. M.; Woerpel, K. A. Organometallics 2010, 29, 1661
2. Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428
3. Nakao, Y.; Yukawa, T.; Hirata, Y.; Oda, S.; Satoh, J.; Hiyama, T. J. Am. Chem. Soc. 2006, 128, 7116
4. Murakami, M.; Ashida, S. Chem. Commun. 2006, 4599
5. Murakami, M.; Ashida, S.; Matsuda, T. J. Am. Chem. Soc. 2005, 127, 6932
6. Okuma, K.; Itoyama, R.; Sou, A.; Nagahora, N.; Shioj, K. Chem. Commun. 2012, 48, 11145
7. Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5340
8. Tambar, U. K.; Ebner, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 11752
9. Islam, M. S.; Brennan, C.; Wang, Q.; Hossain, M. M. J. Org. Chem. 2006, 71, 4675
10. Dudley, M. E.; Morshed, M. M.; Brennan, C. L.; Islam, M. S.; Ahmad, M. S.; Atuu, M.-R.; Branstetter, B.; Hossain, M. M. J. Org. Chem. 2004, 69, 7599
11. Dudley, M. E.; Morshed, M. M.; Hossain, M. M. Synthesis 2006, 1711
12. Mahmood, S. J.; Hossain, M. M. J. Org. Chem. 1998, 63, 3333
13. Kanemasa, S.; Kanai, T.; Araki, T.; Wada, E. Tetrahedron Lett. 1999, 40, 5055
14. Benito-Garagorri, D.; Wiedermann, J.; Pollak, M.; Mereiter, K.; Kirchner, K. Organometallics 2007, 26, 217
15. Alves, L. G.; Dazinger, G.; Veiros, L. F.; Kirchner, K. Eur. J. Inorg. Chem. 2010, 3160
16. Levesque, P.; Fournier, P.-A. J. Org. Chem. 2010, 75, 7033
17. Fructos, M. R.; Díaz-Requejo, M. M.; Pérez, P. J. Chem. Commun. 2009, 5153
18. Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 2434
19. Moebius, D. C.; Kingsbury, J. S. J. Am. Chem. Soc. 2009, 131, 878
20. Rendina, V. L.; Moebius, D. C.; Kingsbury, J. S. Org. Lett. 2011, 13, 2004
21. Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2011, 133, 8834
22. Li, W.; Liu, X.; Hao, X.; Cai, Y.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2012, 51, 8644
23. Xia, Y.; Qu, P.; Liu, Z.; Ge, R.; Xiao, Q.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2013, 52, 2543
24. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258
25. Holmquist, C. R.; Roskamp, E. J. Tetrahedron Lett. 1992, 33, 1131
26. Padwa, A.; Hornbuckle, S. F.; Zhang, Z.; Zhi, L. J. Org. Chem. 1990, 55, 5297
27. Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 9085
28. Bartrum, H. E.; Blakemore, D. C.; Moody, C. J.; Hayes, C. J. J. Org. Chem. 2010, 75, 8674
29. Bandyopadhyay, A.; Agrawal, N.; Mali, S. M.; Jadhav, S. V.; Gopi, H. N. Org. Biomol. Chem. 2010, 8, 4855
30. Yadav, J. S.; Subba Reddy, B. V.; Eeshwaraiah, B.; Reddy, P. N. Tetrahedron 2005, 61, 875
31. Murata, H.; Ishitani, H.; Iwamoto, M. Tetrahedron Lett. 2008, 49, 4788
32. Zhang, Y.; Wang, J. Chem. Commun. 2009, 5350
33. Hashimoto, T.; Miyamoto, H.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 11280
34. Li, W.; Wang, J.; Hu, X.; Shen, K.; Wang, W.; Chu, Y.; Lin, L.; Liu, X.; Feng, X. J. Am. Chem. Soc. 2010, 132, 8532
35. Gao, L.; Kang, B. C.; Hwang, G.-S.; Ryu, D. H. Angew. Chem., Int. Ed. 2012, 51, 8322
36. Hawner, C.; Alexakis, A. Chem. Commun. 2010, 46, 7295
37. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593
38. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388
39. Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105
40. Trost, B. M.; Jiang, C. Synthesis 2006, 369
41. Christoffers, J.; Baro, A. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Wiley-VCH: Weinheim, 2005.
42. Corey, E. J. Angew. Chem., Int. Ed. 2009, 48, 2100
43. Senapati, B. K.; Hwang, G.-S.; Lee, S.; Ryu, D. H. Angew. Chem., Int. Ed. 2009, 48, 4398
44. Lee, S. I.; Hwang, G.-S.; Ryu, D. H. J. Am. Chem. Soc. 2013, 135, 7126
45. Lee, S. I.; Kang, B. C.; Hwang, G.-S.; Ryu, D. H. Org. Lett. 2013, 15, 1428
46. Senapati, B. K.; Gao, L.; Lee, S. I.; Hwang, G.-S.; Ryu, D. H. Org. Lett. 2010, 12, 5088
47. Rapoport, B. H.; Batcho, A. D.; Gordon, J. E. J. Am. Chem. Soc. 1958, 80, 5767
48. Sun, X.; Frimpong, K.; Tan, K. L. J. Am. Chem. Soc. 2010, 132, 11841
49. Arzel, P.; Freida, V.; Weber, P.; Fadel, A. Tetrahedron: Asymmetry 1999, 10, 3877
50. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384
51. Gao, L.; Hwang, G.-S.; Lee, M. Y.; Ryu, D. H. Chem. Commun. 2009, 5460
52. Gao, L.; Hwang, G.-S.; Ryu, D. H. J. Am. Chem. Soc. 2011, 133, 20708
53. Waters, M. L. Curr. Opin. Chem. Biol. 2002, 6, 736
54. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651
55. Salonen, L. M.; Ellermann, M.; Diederich, F. Angew. Chem., Int. Ed. 2011, 50, 4808
56. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525
57. Polar solvent, propionitrile enhances π-π interaction (Table 1, entries 1 and 2), see: ref 10c and Cubberley, M. S.; Iverson, B. L. J. Am. Chem. Soc. 2001, 123, 7560
58. Murphy, K. E.; Hoveyda, A. H. Org. Lett. 2005, 7, 1255
59. Weiner, B.; Szymański, W.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L. Chem. Soc. Rev. 2010, 39, 1656
60. Enantioselective Synthesis of β-Amino Acids, 2 nd ed.; Juaristi, E.; Soloshonok, V. A., Eds.; Wiley: New York, 2005.
61. Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991
62. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091
63. Hong, S.; Lee, J.; Kim, M.; Park, Y.; Park, C.; Kim, M.-h.; Jew, S.-s.; Park, H.-g. J. Am. Chem. Soc. 2011, 133, 4924
64. Zagulyaeva, A. A.; Banek, C. T.; Yusubov, M. S.; Zhdankin, V. V. Org. Lett. 2010, 12, 4644
65. Clayden, J.; Donnard, M.; Lefranc, J.; Tetlow, D. J. Chem. Commun. 2011, 47, 4624
66. Nájera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584
67. Mosey, R. A.; Fisk, J. S.; Tepe, J. J. Tetrahedron: Asymmetry 2008, 19, 2755