Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-α-phenyldimethylsilyl( ddiisopinocampheyl)-crotylborane

Tetrahedron

Volumn 69, Issue 26, 2013, Pages 5468-5475

  Chen, Ming ^a   Roush, William R ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Curtin Hammett control; Enantiodivergent hydroboration; Mismatched double asymmetric crotylboration

Indexed keywords

ALCOHOL; BORANE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; ENANTIOSELECTIVITY; HYDROBORATION; PRIORITY JOURNAL;

EID: 84878251970     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.098     Document Type: Article

References (79)

1. W.R. Roush B.M. Trost, Comprehensive Organic Synthesis Vol. 2 1991 Pergamon Oxford, UK 1
2. Y. Yamamoto, and N. Asao Chem. Rev. 93 1993 2207
3. S.E. Denmark, and N.G. Almstead J. Otera, Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim, Germany 299
4. S.R. Chemler, and W.R. Roush J. Otera, Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim, Germany 403
5. S.E. Denmark, and J. Fu Chem. Rev. 103 2003 2763
6. H. Lachance, and D.G. Hall Org. React. 73 2008 1
7. M. Yus, J.C. Gonzáles-Gómez, and F. Foubelo Chem. Rev. 111 2011 7774
8. J. Pietruszka, and N. Schone Angew. Chem., Int. Ed. 42 2003 5638
9. N.F. Pelz, A.R. Woodward, H.E. Burks, J.D. Sieber, and J.P. Morken J. Am. Chem. Soc. 126 2004 16328
10. J.D. Sieber, and J.P. Morken J. Am. Chem. Soc. 128 2006 74
11. H. Ito, S. Ito, Y. Sasaki, K. Matsuura, and M. Sawamura J. Am. Chem. Soc. 129 2007 14856
12. F. Peng, and D.G. Hall J. Am. Chem. Soc. 129 2007 3070
13. M. Chen, and W.R. Roush Org. Lett. 12 2010 2706
14. M. Althaus, A. Mahmood, J.R. Suarez, S.P. Thomas, and V.K. Aggarwal J. Am. Chem. Soc. 132 2010 4025
15. L.T. Kliman, S.N. Mlynarski, G.E. Ferris, and J.P. Morken Angew. Chem., Int. Ed. 51 2012 521
16. G.E. Ferris, K. Hong, I.A. Roundtree, and J.P. Morken J. Am. Chem. Soc. 135 2013 2501
17. For a recently review on allenes in asymmetric synthesis: S. Yu, and S. Ma Angew. Chem., Int. Ed. 51 2012 3074
18. M. Chen, and W.R. Roush J. Am. Chem. Soc. 133 2011 5744
19. M. Chen, D.H. Ess, and W.R. Roush J. Am. Chem. Soc. 132 2010 7881
20. J.-L. Han, M. Chen, and W.R. Roush Org. Lett. 14 2012 3028
21. H. Sun, J.R. Abbott, and W.R. Roush Org. Lett. 13 2011 2734
22. M. Yin, and W.R. Roush Tetrahedron 67 2011 10274
23. M. Chen, and W.R. Roush Org. Lett. 14 2012 426
24. M. Chen, and W.R. Roush Org. Lett. 14 2012 1556
25. M. Chen, and W.R. Roush Org. Lett. 14 2012 1880
26. M. Chen, and W.R. Roush J. Org. Chem. 78 2013 3
27. M. Chen, and W.R. Roush Org. Lett. 15 2013 1662
28. J.A. Marshall, and K. Maxson J. Org. Chem. 65 2000 630
29. I. Fleming, and D. Waterson J. Chem. Soc., Perkin Trans. 1 1984 1809
30. I. Fleming, T.W. Newton, and F. Roessler J. Chem. Soc., Perkin Trans. 1 1981 2527
31. J.A. Dale, and H.S. Mosher J. Am. Chem. Soc. 95 1973 512
32. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092
33. H.C. Brown, and G. Zweifel J. Am. Chem. Soc. 83 1961 486
34. G. Zweifel, and H.C. Brown J. Am. Chem. Soc. 86 1964 397
35. M. Chen, and W.R. Roush Org. Lett. 13 2011 1992
36. D.D. Davis, and C.E. Gray J. Org. Chem. 35 1970 1303
37. J.M. Jerkunica, and T.G. Traylor J. Am. Chem. Soc. 93 1971 6278
38. S.G. Wierschke, J. Chandrasekhar, and W.L. Jorgensen J. Am. Chem. Soc. 107 1985 1496
39. J.B. Lambert, G.T. Wang, and R.B. Finzel J. Am. Chem. Soc. 109 1987 7838
40. J.B. Lambert, G.T. Wang, and D.H. Teramura J. Org. Chem. 53 1988 5422
41. P. Stewart, M. Chen, W.R. Roush, and D. Ess Org. Lett. 13 2011 1478
42. S. Masamune, W. Choy, J.S. Petersen, and L.R. Sita Angew. Chem., Int. Ed. Engl. 24 1985 1
43. H.C. Brown, and K.S. Bhat J. Am. Chem. Soc. 108 1986 293
44. R.W. Hoffmann Angew. Chem., Int. Ed. Engl. 26 1987 489
45. R.W. Hoffmann, G. Dahmann, and M.W. Andersen Synthesis 1994 629
46. S.R. Chemler, and W.R. Roush J. Org. Chem. 63 1998 3800
47. S.R. Chemler, and W.R. Roush J. Org. Chem. 83 2003 1319
48. M. Chen, and W.R. Roush J. Am. Chem. Soc. 134 2012 3925
49. D.J. Peterson J. Org. Chem. 33 1968 780
50. D.J. Ager Org. React. 38 1990 1
51. K.G. Hancock, and J.D. Kramer J. Am. Chem. Soc. 95 1973 6463
52. G.W. Kramer, and H.C. Brown J. Organomet. Chem. 132 1977 9
53. R.W. Hoffmann, and H.J. Zeiss J. Org. Chem. 46 1981 1309
54. U. Henriksen, J.P. Snyder, and T.A. Halgren J. Org. Chem. 46 1981 3767
55. K.K. Wang, Y.G. Gu, and C. Liu J. Am. Chem. Soc. 112 1990 4424
56. G.Y. Fang, and V.K. Aggarwal Angew. Chem., Int. Ed. 46 2007 359
57. E. Canales, A.Z. González, and J.A. Soderquist Angew. Chem., Int. Ed. 46 2007 397
58. J. Kister, A.C. DeBaillie, R. Lira, and W.R. Roush J. Am. Chem. Soc. 131 2009 14174
59. M. Chen, M. Handa, and W.R. Roush J. Am. Chem. Soc. 131 2009 14602
60. D.H. Ess, J. Kister, M. Chen, and W.R. Roush Org. Lett. 11 2009 5538
61. J.I. Seeman Chem. Rev. 83 1983 83
62. J. Halpern Science 217 1982 401
63. C.R. Landis, and J. Halpern J. Am. Chem. Soc. 109 1987 1746
64. W.R. Roush J. Org. Chem. 56 1991 4151
65. M. Cherest, H. Felkin, and N. Prudent Tetrahedron Lett. 18 1968 2199
66. N.T. Anh, and O. Eisenstein Nouv. J. Chim. 1 1977 61
67. T.A. Blumenkopf, and L.E. Overman Chem. Rev. 86 1986 857
68. I. Fleming Org. React. 37 1989 57
69. I. Fleming, A. Barbero, and D. Walter Chem. Rev. 97 1997 2063
70. K. Miura, and A. Hosomi Synlett 2003 143
71. C.-M. Yu, J. Youn, and H.-K. Jung Bull. Korean Chem. Soc. 27 2006 463
72. D.A. Evans, and Y. Aye J. Am. Chem. Soc. 128 2006 11034
73. E.A. Ilardi, C.E. Stivala, and A. Zakarian Org. Lett. 10 2008 1727
74. Y. Nishimoto, M. Kajioka, T. Saito, M. Yasuda, and A. Baba Chem. Commun. 2008 6396
75. R.H. Bates, M. Chen, and W.R. Roush Curr. Opin. Drug Discovery Dev. 11 2008 778
76. K. Aikawa, Y.-T. Hioki, and K. Mikami J. Am. Chem. Soc. 131 2009 13922
77. S.E. Denmark, and J.H.-C. Liu Angew. Chem., Int. Ed. 49 2010 2978
78. S.E. Denmark, and R.F. Sweis A. de Meijere, F. Diederich, Metal Catalyzed Cross-coupling Reactions 2nd ed. 2004 Wiley-VCH Weinheim, Germany Chapter 4
79. T. Hiyama F. Diederich, P.J. Stang, Metal Catalyzed Cross-coupling Reactions 1998 Wiley-VCH Weinheim, Germany Chapter 10 and references cited therein