Iminopyridine oxazoline iron catalyst for asymmetric hydroboration of 1,1-disubtituted aryl alkenes

Organic Letters

Volumn 16, Issue 24, 2014, Pages 6452-6455

  Chen, Jianhui ^a   Xi, Tuo ^a   Lu, Zhan ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84919628631     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503282r     Document Type: Article

References (48)

1. Brown, H. C. Organic Synthesis via Boranes; Wiley Interscience: New York, 1975.
2. Brown, H. C.; Singaram, B. Pure Appl. Chem. 1987, 59, 879
3. Bubnov, Y. In Science of Synthesis; Kaufmann, D. E.; Matteson, D. S., Eds.; Georg Thieme Verlag Stuttgart: New York, 2004; Vol. 6, pp 945-1072.
4. Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
5. Doucet, H. Eur. J. Org. Chem. 2008, 2013
6. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
7. Scott, H. K.; Aggarwal, V. K. Chem. - Eur. J. 2011, 17, 13124
8. Stymiest, J. L.; Bagutski, V.; French, R. M.; Aggarwal, V. K. Nature 2008, 456, 778
9. Bagutski, V.; French, R. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2010, 49, 5142
10. Bonet, A.; Odachowski, M.; Leonori, D.; Essafi, S.; Aggarwal, V. K. Nat. Chem. 2014, 6, 584
11. Brown, H. C.; Singaram, B. Acc. Chem. Res. 1988, 21, 287
12. Zaidlewicz, M. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982, and references cited therein.
13. Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486
14. Gonzalez, A. Z.; Román, J. G.; Gonzalez, E.; Martinez, J.; Medina, J. R.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2008, 130, 9218
15. Thomas, S. P.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2009, 48, 1896
16. Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426
17. Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179
18. Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957
19. Doucet, H.; Fernandez, E.; Layzell, T. P.; Brown, J. M. Chem. - Eur. J. 1999, 5, 1320
20. Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695
21. Crudden, C. M.; Hleba, Y. B.; Chen, A. C. J. Am. Chem. Soc. 2004, 126, 9200
22. Moteki, S. A.; Wu, D.; Chandra, K. L.; Reddy, D. S.; Takacs, J. M. Org. Lett. 2006, 8, 3097
23. Moteki, S. A.; Takacs, J. M. Angew. Chem., Int. Ed. 2008, 47, 894
24. Crudden, C. M.; Glasspoole, B. W.; Lata, C. J. Chem. Commun. 2009, 6704
25. Moteki, S. A.; Toyama, K.; Liu, Z.; Ma, J.; Holmes, A. E.; Takacs, J. M. Chem. Commun. 2012, 48, 263
26. Hayashi, T.; Matsumoto, Y. Tetrahedron: Asymmetry 1991, 2, 601
27. Mazet, C.; Gerard, D. Chem. Commun. 2011, 47, 298
28. Corberan, R.; Mszar, N. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2011, 50, 7079
29. Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217
30. Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500
31. Gopalaiah, K. Chem. Rev. 2013, 113, 3248
32. Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2012, 134, 12370
33. Zuo, W.; Lough, A. J.; Li, Y. F.; Morris, R. H. Science 2013, 342, 1080
34. Deng, Q. H.; Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2013, 135, 5356
35. Liu, G. S.; Zhang, Y. Q.; Yuan, Y. A.; Xu, H. J. Am. Chem. Soc. 2013, 135, 3343
36. Zuo, W.; Lough, A. J.; Li, Y. F.; Morris, R. H. Science 2013, 342, 1080
37. Li, Y.; Yu, S.; Wu, X.; Xiao, J.; Shen, W.; Dong, Z.; Gao, J. J. Am. Chem. Soc. 2014, 136, 4031
38. Shaw, S.; White, J. D. J. Am. Chem. Soc. 2014, 136, 13578
39. Lu, D.-F.; Zhu, C.-L.; Jia, Z.-X.; Xu, H. J. Am. Chem. Soc. 2014, 136, 13186
40. Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049
41. Wu, J. Y.; Moreau, B.; Ritter, T. J. J. Am. Chem. Soc. 2009, 131, 12915
42. Chirik, P. J.; Wieghardt, K. Science 2010, 327, 794
43. Obligacion, J. V.; Chirik, P. J. Org. Lett. 2013, 15, 2680
44. Zhang, L.; Peng, D.; Leng, X.; Huang, Z. Angew. Chem., Int. Ed. 2013, 52, 3676
45. Greenhalgh, M. D.; Thomas, S. P. Chem. Commun. 2013, 49, 11230
46. Bart, S. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2004, 126, 13794
47. Unfortunately, during the time we were submitting the manuscript on our independent work, a similar result was reported by Zhang, L.; Zuo, Z.-Q.; Wan, X.-L.; Huang, Z. J. Am. Chem. Soc. 2014, 136, 15501. However, since November 14th, 2013, we used a different strategy for the synthesis of chiral iminopyridine oxazoline.
48. CCDC number is 1029987.