Copper-catalyzed boration of activated alkynes. Chiral boranes via a one-pot copper-catalyzed boration and reduction protocol

Tetrahedron

Volumn 68, Issue 17, 2012, Pages 3444-3449

  Jung, Ho Young ^a   Feng, Xinhui ^a   Kim, Hyohyun ^a   Yun, Jaesook ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Asymmetric synthesis; Boration; Conjugate reduction; Copper; Vinylboronates

Indexed keywords

2 [2 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PROP 1 ENYL]BENZO[D]OXAZOL; 2 [2 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PROPYL]BENZO[D]OXAZOLE; 4,4,5,5 TETRAMETHYL 2 STYRYL 1,3,2 DIOXABOROLANE; ALKYNE; BORANE DERIVATIVE; COPPER; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)ACRYLATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)BUT 2 ENOATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)BUTANOATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)OCT 2 ENOATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)OCTANOATE; ETHYL 3 CYCLOHEXYL 3 (4,4,5,5, TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)ACRYLATE; ETHYL 4 (TETRAHYDRO 2H PYRAN 2 YLOXY) 3(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)BUT 2 ENOATE; ETHYL 4 CYCLOHEXYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)BUT 2 ENOATE; ETHYL 4 CYCLOHEXYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)BUTANOATE; ETHYL 4 METHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PENTANOATE; ETHYL 4,4 DIMETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PEN 2 ENOATE; ETHYL 5 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PENTANOATE; PHOSPHINE; UNCLASSIFIED DRUG;

ADDITION REACTION; BORATION; CATALYST; CHEMICAL MODIFICATION; CONFERENCE PAPER; ONE POT SYNTHESIS; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY;

EID: 84859545984     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.061     Document Type: Conference Paper

References (72)

1. I. Beletskaya, and C. Moberg Chem. Rev. 106 2006 2320 2354
2. G.J. Irvine, M.J.G. Lesley, T.B. Marder, N.C. Norman, C.R. Rice, E.G. Robins, W.R. Roper, G.R. Whittell, and L.J. Wright Chem. Rev. 98 1998 2685 2722
3. M.G. Davison, A.K. Hughes, T.B. Marder, and K. Wade Contemporary Boron Chemistry 2000 RSC
4. D.S. Matteson Stereodirected Synthesis with Organoboranes 1995 Springer
5. M. Suginome, T. Matsuda, T. Ohmura, A. Seki, and M. Murakami R.H. Crabtree, D.M.P. Mingos, Comprehensive Organometallic Chemistry III Vol. 10 2007 Elsevier 725 787
6. K. Takahashi, T. Ishiyama, and N. Miyaura J. Organomet. Chem. 625 2001 47 53
7. M. Gao, S.B. Thorpe, and W.L. Santos Org. Lett. 11 2009 3478 3481
8. H. Chea, H.-S. Sim, and J. Yun Bull. Korean Chem. Soc. 31 2010 551 552
9. Pt: Y.G. Lawson, M.J.G. Lesley, T.B. Marder, N.C. Norman, and C.R. Rice Chem. Commun. 1997 2051 2052
10. N.J. Bell, A.J. Cox, N.R. Cameron, J.S.O. Evans, T.B. Marder, M.A. Duin, C.J. Elsevier, X. Baucherel, A.A.D. Tulloch, and R.P. Tooze Chem. Commun. 2004 1854 1855
11. Rh: G.W. Kabalka, B.C. Das, and S. Das Tetrahedron Lett. 43 2002 2323 2325
12. Ni: K. Hirano, H. Yorimitsu, and K. Oshima Org. Lett. 9 2007 5031 5033
13. NHC: K. Lee, A.R. Zhugralin, and A.H. Hoveyda J. Am. Chem. Soc. 131 2009 7253 7255
14. S. Mun, J.-E. Lee, and J. Yun Org. Lett. 8 2006 4887 4889
15. H.-S. Sim, X. Feng, and J. Yun Chem. - Eur. J. 15 2009 1939 1943
16. L. Dang, Z. Lin, and T.B. Marder Organometallics 27 2008 4443 4454
17. R.E. Shade, A.M. Hyde, J.-C. Olsen, and C.A. Merlic J. Am. Chem. Soc. 132 2010 1202 1203
18. Q. Wang, and M.G. Finn Org. Lett. 2 2000 4063 4065
19. S.-J. Jeon, Y.K. Chen, and P.J. Walsh Org. Lett. 7 2005 1729 1732
20. E. Hupe, I. Marek, and P. Knochel Org. Lett. 4 2002 2861 2863
21. A.D. Schlüter J. Polym. Sci., Part A: Polym. Chem. 39 2001 1533 1556
22. H.A. Stefani, R. Cella, and A.S. Vieira Tetrahedron 63 2007 3623 3658
23. T. Ohmura, Y. Yamamoto, and N. Miyaura J. Am. Chem. Soc. 122 2000 4990 4991
24. C.E. Tucker, J. Davidson, and P. Knochel J. Org. Chem. 57 1992 3482 3485
25. S. Pereira, and M. Srebnik Organometallics 14 1995 3127 3128
26. S. Pereira, and M. Srebnik Tetrahedron Lett. 37 1996 3283 3286
27. Y.D. Wang, G. Kimball, A.S. Prashad, and Y. Wang Tetrahedron Lett. 46 2005 8777 8780
28. I.D. Gridnev, N. Miyaura, and A. Suzuki Organometallics 12 1993 589 592
29. T. Ishiyama, J. Takagi, A. Kamon, and N. Miyaura J. Organomet. Chem. 687 2003 284 290
30. J. Takagi, K. Takahashi, T. Ishiyama, and N. Miyaura J. Am. Chem. Soc. 124 2002 8001 8006
31. E.-i. Negishi, and T. Yoshida J. Am. Chem. Soc. 95 1973 6837 6838
32. P. Martinez-Fresneda, and M. Vaultier Tetrahedron Lett. 30 1989 2929 2932
33. J. Plamondon, J.T. Snow, and G. Zweifel Organomet. Chem. Synth. 1 1971 249 252
34. J.-E. Lee, J. Kwon, and J. Yun Chem. Commun. 2009 5996 5998
35. H. Chea, H.-S. Sim, and J. Yun Adv. Synth. Catal. 351 2009 855 858
36. X. Feng, and J. Yun Chem. Commun. 2009 6577 6579
37. X. Feng, and J. Yun Chem. - Eur. J. 16 2010 13609 13612
38. V. Lillo, A. Prieto, A. Bonet, M.M. Díaz-Requejo, J. Ramírez, P.J. Pérez, and E. Fernández Organometallics 28 2009 659 662
39. I.-H. Chen, L. Yin, W. Itano, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 131 2009 11664 11665
40. J.M. O'Brien, K. Lee, and A.H. Hoveyda J. Am. Chem. Soc. 132 2010 10630 10633
41. Rh: T. Shiomi, T. Adachi, K. Toribatake, L. Zhou, and H. Nishiyama Chem. Commun. 2009 5987 5989
42. Ni: V. Lillo, M.J. Geier, S.A. Westcott, and E. Fernández Org. Biomol. Chem. 7 2009 4674 4676
43. Phosphine: A. Bonet, H. Gulyás, and E. Fernández Angew. Chem., Int. Ed. 49 2010 5130 5134
44. D.H. Appella, Y. Moritani, R. Shintani, E.M. Ferreira, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 9473 9474
45. B.H. Lipshutz, K. Noson, and W. Chrisman J. Am. Chem. Soc. 123 2001 12917 12918
46. C. Czekelius, and E.M. Carreira Angew. Chem., Int. Ed. 42 2003 4793 4795
47. D. Lee, D. Kim, and J. Yun Angew. Chem., Int. Ed. 45 2006 2785 2787
48. K. Yoo, H. Kim, and J. Yun Chem. - Eur. J. 15 2009 11134 11138
49. T. Llamas, R.G. Arrayás, and J.C. Carretero Angew. Chem., Int. Ed. 46 2007 1 5
50. J.-N. Desrosiers, and A.B. Charette Angew. Chem., Int. Ed. 46 2007 5955 5957
51. C. Deutsch, N. Krause, and B.H. Lipshutz Chem. Rev. 108 2008 2916 2927
52. With an alkynoester, double reduction was reported to form the saturated ester derivative with CuH, see: B.H. Lipshutz Synlett 2009 509 524
53. E.J. Corey, and J.A. Katzenellenbogen J. Am. Chem. Soc. 91 1969 1851 1852
54. For anti-addition examples in copper-mediate additions when t-Bu is involved: J.M. Gil, and D.Y. Oh J. Org. Chem. 64 1999 2950 2953
55. H.R. Kim, and J. Yun Chem. Commun. 2011 2943 2945
56. D.S. Matteson Chem. Rev. 89 1989 1535 1551
57. C.M. Crudden, and D. Edwards Eur. J. Org. Chem. 2003 4695 4712
58. D. Imao, B.W. Glasspoole, V.S. Laberge, and C.M. Crudden J. Am. Chem. Soc. 131 2009 5024 5025
59. A. Ros, and V.K. Aggarwal Angew. Chem., Int. Ed. 48 2009 6289 6292
60. T. Ohmura, T. Awano, and M. Suginome J. Am. Chem. Soc. 132 2010 13191 13193
61. D.L. Sandrock, L. Jean-Gérard, C. Chen, S.D. Dreher, and G.A. Molander J. Am. Chem. Soc. 132 2010 17108 17110
62. M. Ueda, A. Saitoh, and N. Miyaura J. Organomet. Chem. 642 2002 145 147
63. W.J. Moran, and J.P. Morken Org. Lett. 8 2006 2413 2415
64. A. Paptchikhine, P. Cheruku, M. Engman, and P.G. Andersson Chem. Commun. 2009 5996 5998
65. Copper-catalyzed reduction of β-silylated enoates, see: B.H. Lipshutz, N. Tanaka, B.R. Taft, and C.-T. Lee Org. Lett. 8 2006 1963 1966
66. C.N. Farthing, and S.P. Marsden Tetrahedron Lett. 41 2000 4235 4238
67. L. Rupnicki, A. Saxena, and H.W. Lam J. Am. Chem. Soc. 131 2009 10386 10387
68. D. Lee, and J. Yun Tetrahedron Lett. 45 2004 5415 5417
69. For examples of ligand effect on the copper-catalyzed boron addition to internal aryl alkynes: H.R. Kim, I.G. Jung, K. Yoo, K. Jang, E.S. Lee, J. Yun, and S.U. Son Chem. Commun. 2010 758 760 see also Ref. 15c
70. X.-X. Shi, C.-L. Shen, J.-Z. Yao, L.-D. Nie, and N. Quan Tetrahedron: Asymmetry 21 2010 277 284
71. K. Nagai, T. Doi, T. Sekiguchi, L. Namatame, T. Sunazuka, H. Tomoda, S. mura, and T. Takahashi J. Comb. Chem. 8 2006 103 109
72. S. Sumida, M. Ohga, J. Mitani, and J. Nokami J. Am. Chem. Soc. 122 2000 1310 1313