Regioselective and stereoselective entry to β,β-disubstituted vinyl ethers via the sequential hydroboration/Suzuki-Miyaura coupling of ynol ethers

Journal of Organic Chemistry

Volumn 78, Issue 19, 2013, Pages 9815-9821

  Cui, Weijian ^a   Mao, Mengyi ^a   He, Zuying ^a   Zhu, Gangguo ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL ETHERS; ALKENYL GROUPS; HYDROBORATION; REACTION CONDITIONS; REGIO-SELECTIVE; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; VINYL ETHERS;

CARBON DIOXIDE; FUNCTIONAL GROUPS; STEREOCHEMISTRY; STEREOSELECTIVITY;

ETHERS;

ALDEHYDE DERIVATIVE; ALKENYL GROUP; ALKYL GROUP; ETHER DERIVATIVE; HALIDE; VINYL DERIVATIVE;

ARTICLE; HYDROBORATION; HYDROLYSIS; ONE POT SYNTHESIS; STEREOCHEMISTRY; SUZUKI REACTION;

EID: 84885093747     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401523m     Document Type: Article

References (59)

1. Dehi, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973
2. Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978
3. Willis, M. C.; Taylor, D.; Gillmore, A. T. Chem. Commun. 2003, 2222
4. Alcazar, E.; Pletcher, J. M.; McDonald, F. E. Org. Lett. 2004, 6, 3877
5. Shade, R. E.; Hyde, A. M.; Olsen, J.-C.; Merlic, C. A. J. Am. Chem. Soc. 2010, 132, 1202
6. Winternheimer, D. J.; Merlic, C. A. Org. Lett. 2010, 12, 2508
7. DeBergh, J. R.; Spivey, K. M.; Ready, J. M. J. Am. Chem. Soc. 2008, 130, 7828
8. Song, Z.; Kui, L.; Sun, X.; Li, L. Org. Lett. 2011, 13, 1440
9. Winternheimer, D. J.; Shade, R. E.; Merlic, C. A. Synthesis 2010, 2497 and references therein
10. Whelligan, D. K.; Thomson, D. W.; Taylor, D.; Hoelder, S. J. Org. Chem. 2010, 75, 11
11. Shindo, M.; Kita, T.; Kumagai, T.; Matsumoto, K.; Shishido, K. J. Am. Chem. Soc. 2006, 128, 1062
12. Sosa, J. R.; Tudjarian, A. A.; Minehan, T. G. Org. Lett. 2008, 10, 5091
13. Mak, X. Y.; Ciccolini, R. P.; Robinson, J. M.; Tester, J. W.; Danheiser, R. L. J. Org. Chem. 2009, 74, 9381
14. Davies, P. W.; Cremonesi, A.; Dumitrescu, L. Angew. Chem., Int. Ed. 2011, 50, 8931
15. Komine, Y.; Tanaka, K. Org. Lett. 2010, 12, 1312
16. Mejuch, T.; Botoshansky, M.; Marek, I. Org. Lett. 2011, 13, 3604
17. Tran, V.; Minehan, T. G. Org. Lett. 2011, 13, 6588
18. Tran, V.; Minehan, T. G. Org. Lett. 2012, 14, 6100
19. Verrier, C.; Carret, S.; Poisson, J.-F. Org. Lett. 2012, 14, 5122
20. Moyano, A.; Charbonnier, F.; Greene, A. E. J. Org. Chem. 1987, 52, 2919
21. Levin, A.; Basheer, A.; Marek, I. Synlett 2010, 329
22. Qi, X.; Ready, J. M. Angew. Chem., Int. Ed. 2008, 47, 7068
23. Hashmi, A. S. K.; Rudolph, M.; Huck, J.; Frey, W.; Bats, J. W.; Hamzić, M. Angew. Chem., Int. Ed. 2009, 48, 5848
24. Yamasaki, R.; Terashima, N.; Sotome, I.; Komagawa, S.; Saito, S. J. Org. Chem. 2010, 75, 480
25. Miyauchi, Y.; Noguchi, K.; Tanaka, K. Org. Lett. 2012, 14, 5856
26. Miyauchi, Y.; Kobayashi, M.; Tanaka, K. Angew. Chem., Int. Ed. 2011, 50, 10922
27. Lemoine, P.; Daoust, B. Tetrahedron Lett. 2008, 49, 6175
28. Hanna, R.; Daoust, B. Tetrahedron 2011, 67, 92
29. Chen, X.; Kong, W.; Cai, H.; Kong, L.; Zhu, G. Chem. Commun. 2011, 47, 2164
30. Chen, D.; Cao, Y.; Yuan, Z.; Cai, H.; Zheng, R.; Kong, L.; Zhu, G. J. Org. Chem. 2011, 76, 4071
31. Chen, X.; Chen, D.; Lu, Z.; Kong, L.; Zhu, G. J. Org. Chem. 2011, 76, 6338
32. Lu, Z.; Kong, W.; Yuan, Z.; Zhao, X.; Zhu, G. J. Org. Chem. 2011, 76, 8524
33. Lu, Z.; Xu, X.; Yang, Z.; Kong, L.; Zhu, G. Tetrahedron Lett. 2012, 53, 3433
34. Lu, Z.; Cui, W.; Xia, S.; Bai, Y.; Luo, F.; Zhu, G. J. Org. Chem. 2012, 77, 9871
35. Zhu, G.; Chen, D.; Wang, Y.; Zheng, R. Chem. Commun. 2012, 48, 5796
36. Cai, H.; Yuan, Z.; Zhu, W.; Zhu, G. Chem. Commun. 2011, 47, 8682
37. Bai, Y.; Yin, J.; Kong, W.; Mao, M.; Zhu, G. Chem. Commun. 2013, 49, 7650
38. Satoh, M.; Miyaura, N.; Suzuki, A. Synthesis 1987, 373
39. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
40. Gridnev, I. D.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 5351
41. Miyaura, N.; Maeda, K.; Suginome, H.; Suzuki, A. J. Org. Chem. 1982, 47, 2117
42. Tucker, C. E.; Davidson, J.; Knochel, P. J. Org. Chem. 1992, 57, 3482
43. Brown, H. C.; Campbell, J. B., Jr. Aldrichimica Acta 1981, 14, 3
44. Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957
45. Trost, B. M.; Ball, Z. T. Synthesis 2005, 853 and references therein
46. Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589
47. Ohmura, T.; Yamamoto, Y.; Miyaura, N. J. Am. Chem. Soc. 2000, 122, 4990
48. Hoffmann, R. W.; Krüger, J.; Brückner, D. New J. Chem. 2001, 25, 102
49. Lipshutz, B. H.; Bošković, Z. V.; Aue, D. H. Angew. Chem., Int. Ed. 2008, 47, 10183
50. Semba, K.; Fujihara, T.; Terao, J.; Tsuji, Y. Chem.-Eur. J. 2012, 18, 4179
51. Gunanathan, C.; Hölscher, M.; Pan, F.; Leitner, W. J. Am. Chem. Soc. 2012, 134, 14349
52. Haberberger, M.; Enthaler, S. Chem.-Asian J. 2013, 8, 50
53. Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127
54. Shirakawa, K.; Arase, A.; Hoshi, M. Synthesis 2004, 1814
55. Jouvin, K.; Bayle, A.; Legrand, F.; Evano, G. Org. Lett. 2012, 14, 1652
56. Tanaka, R.; Miller, S. I. Tetrahedron Lett. 1971, 12, 1753
57. Lessi, M.; Masini, T.; Nucara, L.; Bellina, F.; Rossi, R. Adv. Synth. Catal. 2011, 353, 501
58. Barluenga, J.; Escribano, M.; Moriel, P.; Aznar, F.; Valdés, C. Chem.-Eur. J. 2009, 15, 13291
59. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217