Regio- and enantioselective copper(I)-catalyzed hydroboration of borylalkenes: Asymmetric synthesis of 1,1-diborylalkanes

Angewandte Chemie - International Edition

Volumn 52, Issue 14, 2013, Pages 3989-3992

  Feng, Xinhui ^a   Jeon, Heekyung ^a   Yun, Jaesook ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

1,1 diborylalkanes; copper; enantioselectivity; hydroboration; regioselectivity

Indexed keywords

1,1-DIBORYLALKANES; ASYMMETRIC SYNTHESIS; BISPHOSPHINE; ENANTIOSELECTIVE; HYDROBORATION; STERIC PROPERTIES; STYRENE DERIVATIVES; SUBSTITUTED ALKENE;

COPPER; REGIOSELECTIVITY; STYRENE;

ENANTIOSELECTIVITY;

EID: 84875744658     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201208610     Document Type: Article

References (58)

1. D. Männig, H. Nöth, Angew. Chem. 1985, 97, 854-855
2. Angew. Chem. Int. Ed. Engl. 1985, 24, 878-879; for reviews, see
3. K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191
4. C. M. Crudden, D. Edwards, Eur. J. Org. Chem. 2003, 4695-4712.
5. A.-M. Carroll, T. P. O'Sullivan, P. J. Guiry, Adv. Synth. Catal. 2005, 347, 609-631
6. T. Hayashi, Y. Matsumoto, Y. Ito, Tetrahedron: Asymmetry 1991, 2, 601-612
7. C. M. Crudden, Y. B. Hleba, A. C. Chen, J. Am. Chem. Soc. 2004, 126, 9200-9201
8. S. A. Moteki, D. Wu, K. L. Chandra, D. S. Reddy, J. M. Takacs, Org. Lett. 2006, 8, 3097-3100
9. K. Endo, M. Hirokami, T. Shibata, Organometallics 2008, 27, 5390-5393
10. M. Rubina, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc. 2003, 125, 7198-7199.
11. D. Noh, H. Chea, J. Ju, J. Yun, Angew. Chem. 2009, 121, 6178-6180
12. Angew. Chem. Int. Ed. 2009, 48, 6062-6064
13. D. Noh, S. K. Yoon, J. Won, J. Y. Lee, J. Yun, Chem. Asian J. 2011, 6, 1967-1969; for early examples of copper-catalyzed hydroboration of C=N and C=C bonds with catecholborane, see
14. R. T. Baker, J. C. Calabrese, S. A. Westcott, J. Organomet. Chem. 1995, 498, 109-117
15. V. Lillo, M. R. Fructos, J. Ramírez, A. A. C. Braga, F. Maseras, M. M. Díaz-Requejo, P. J. Pérez, E. Fernández, Chem. Eur. J. 2007, 13, 2614-2621.
16. T. Kurahashi, T. Hata, H. Masai, H. Kitagawa, M. Shimizu, T. Hiyama, Tetrahedron 2002, 58, 6381-6395
17. M. Shimizu, C. Nakamaki, K. Shimono, M. Schelper, T. Kurahashi, T. Hiyama, J. Am. Chem. Soc. 2005, 127, 12506-12507
18. N. Iwadate, M. Suginome, J. Am. Chem. Soc. 2010, 132, 2548-2549
19. R. B. Coapes, F. E. S. Souza, R. L. Thomas, J. J. Hall, T. B. Marder, Chem. Commun. 2003, 614-615
20. J. Takaya, N. Iwasawa, ACS Catal. 2012, 2, 1993-2006
21. M. Tobisu, N. Chatani, Angew. Chem. 2009, 121, 3617-3620
22. Angew. Chem. Int. Ed. 2009, 48, 3565-3568.
23. K. Endo, T. Ohkubo, M. Hirokami, T. Shibata, J. Am. Chem. Soc. 2010, 132, 11033-11035
24. J. C. H. Lee, R. McDonald, D. G. Hall, Nat. Chem. 2011, 3, 894-899.
25. M. Shimizu, M. Schelper, I. Nagao, K. Shimono, T. Kurahashi, T. Hiyama, Chem. Lett. 2006, 35, 1222-1223
26. K. Endo, M. Hirokami, T. Shibata, J. Org. Chem. 2010, 75, 3469-3472
27. K. Endo, M. Hirokami, T. Shibata, Synlett 2009, 1331-1335.
28. D. J. Pasto, J. Am. Chem. Soc. 1964, 86, 3039-3047
29. P. Nguyen, R. B. Coapes, A. D. Woodward, N. J. Taylor, J. M. Burke, J. A. K. Howard, T. B. Marder, J. Organomet. Chem. 2002, 652, 77-85
30. V. V. R. Rao, S. K. Agarwal, I. Mehrotra, D. Devaprabhakara, J. Organomet. Chem. 1979, 166, 9-16
31. H. C. Brown, C. G. Scouten, R. Liotta, J. Am. Chem. Soc. 1979, 101, 96-99.
32. C. Wiesauer, W. Weissensteiner, Tetrahedron: Asymmetry 1996, 7, 5-8; for regioselective formation of 1,2-diboronate by borylcupration, see
33. Y. Lee, H. Jang, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 18234-18235
34. H.-Y. Jung, J. Yun, Org. Lett. 2012, 14, 2606-2609.
35. S. Mun, J.-E. Lee, J. Yun, Org. Lett. 2006, 8, 4887-4889
36. J.-E. Lee, J. Yun, Angew. Chem. 2008, 120, 151-153
37. Angew. Chem. Int. Ed. 2008, 47, 145-147
38. H.-S. Sim, X. Feng, J. Yun, Chem. Eur. J. 2009, 15, 1939-1943
39. H. Chea, H.-S. Sim, J. Yun, Adv. Synth. Catal. 2009, 351, 855-858
40. X. Feng, J. Yun, Chem. Commun. 2009, 6577-6579
41. I.-H. Chen, L. Yin, W. Itano, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 11664-11665
42. J. M. O'Brien, K.-s. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 10630-10663
43. X. Feng, J. Yun, Chem. Eur. J. 2010, 16, 13609-13612.
44. K. Sasaki, T. Hayashi, Angew. Chem. 2010, 122, 8321-8323
45. Angew. Chem. Int. Ed. 2010, 49, 8145-8147.
46. D. G. Hall, in Boronic acids, 2nd ed., (Ed.: D. G. Hall,), Wiley, Weinheim, 2011, chap. 1
47. H. Noguchi, K. Hojo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 758-759.
48. J. Won, D. Noh, J. Yun, J. Y. Lee, J. Phys. Chem. A 2010, 114, 12112-12115.
49. D. Zhao, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 14440-14441
50. Y. Du, L.-W. Xu, Y. Shimizu, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 16146-16147
51. B. H. Lipshutz, Ž. V. Boškovič, D. H. Aue, Angew. Chem. 2008, 120, 10337-10340
52. Angew. Chem. Int. Ed. 2008, 47, 10183-10186
53. H. Kim, J. Yun, Adv. Synth. Catal. 2010, 352, 1881-1885; for theoretical DFT calculations of related mechanisms, see also Ref. [3b] and [13].
54. Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 3160-3161
55. R. Corberán, N. W. Mszar, A. H. Hoveyda, Angew. Chem. 2011, 123, 7217-7220
56. Angew. Chem. Int. Ed. 2011, 50, 7079-7082.
57. T. Ohmura, T. Awano, M. Suginome, J. Am. Chem. Soc. 2010, 132, 13191-13193
58. D. Sandrock, L. Jean-Gérard, C. Chen, S. D. Dreher, G. A. Molander, J. Am. Chem. Soc. 2010, 132, 17108-17110.