Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF 3·OEt 2

Tetrahedron

Volumn 68, Issue 32, 2012, Pages 6463-6471

  Ertürk, Erkan ^a   Tezeren, Mustafa A ^a,b   Atalar, Taner ^a   Tilki, Tahir ^b  

^a MATERIALS INSTITUTE   (Turkey)

^b SULEYMAN DEMIREL UNIVERSITY   (Turkey)

Author keywords

BF 3 OEt 2; Catalytic TMEDA; DoM; Epoxide opening; Ortho lithiation

Indexed keywords

ANISOLE DERIVATIVE; BORON TRIFLUORIDE; EPOXIDE; ETHER; ETHYLENEDIAMINE DERIVATIVE; LEWIS ACID; N,N,N',N' TETRAMETHYLETHYLENEDIAMINE; NUCLEOPHILE; ORTHO LITHIOANISOLE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; HYDROLYSIS KINETICS; LITHIATION; MASS FRAGMENTOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; RING OPENING; STOICHIOMETRY; TEMPERATURE;

EID: 84862771920     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.05.116     Document Type: Article

References (97)

1. J.G. Smith Synthesis 1984 629 656
2. A.K. Yudin Aziridines and Epoxides 2006 Wiley-VCH Weinheim
3. S.K. Taylor Tetrahedron 56 2000 1149 1163
4. M. Pineschi Eur. J. Org. Chem. 2006 4979 4988
5. S.H. Krake, and S.C. Bergmeier Tetrahedron 66 2010 7337 7360
6. K. Imi, N. Yanagihara, and K. Utimoto J. Org. Chem. 52 1987 1013 1016
7. M.K. Sassaman, G.K.S. Prakash, and G.A. Olah J. Org. Chem. 55 1990 2016 2018
8. M. Chini, P. Crotti, L. Favero, and F. Macchia Tetrahedron Lett. 32 1991 4775 4778
9. D. Mitchell, and T.M. Koenig Tetrahedron Lett. 33 1992 3281 3284
10. J.A. Ciaccio, C. Stanescu, and J. Bontemps Tetrahedron Lett. 33 1992 1431 1434
11. H. Ohno, A. Mori, and S. Inoue Chem. Lett. 1993 975 978
12. J.A. Ciaccia, M. Smrtka, W.A. Maio, and D. Rucando Tetrahedron Lett. 45 2004 7201 7204
13. B. Mirmashhori, N. Azizi, and M.R. Saidi J. Mol. Catal. A: Chem. 247 2006 159 161
14. A. Procopio, P. Costanzo, R. Dalpozzo, L. Maiuolo, M. Nardi, and M. Oliverio Tetrahedron Lett. 51 2010 5150 5153
15. B.M. Cole, K.D. Shimizu, C.A. Krueger, J.P.A. Harrity, M.L. Snapper, and A.H. Hoveyda Angew. Chem., Int. Ed. 35 1996 1668 1671
16. S.E. Schaus, and E.N. Jacobsen Org. Lett. 2 2000 1001 1004
17. B. Saha, M.-H. Lin, and T.V. RajanBabu J. Org. Chem. 72 2007 8648 8655
18. Y.N. Belokon, D. Chusov, A.S. Peregudov, L.V. Yashkina, G.I. Timofeeva, V.I. Maleev, M. North, and H.B. Kagan Adv. Synth. Catal. 351 2009 3157 3167
19. R.C. Huston, and H.E. Tiefenthal J. Org. Chem. 16 1951 673 678
20. C. Huynh, F. Derguini-Boumechal, and G. Linstrumelle Tetrahedron Lett. 20 1979 1503 1506
21. K. Couture, V. Gouverneur, and C. Mioskowski Bioorg. Med. Chem. Lett. 9 1999 3023 3026
22. T. Tanaka, K. Hiramatsu, Y. Kobayashi, and H. Ohno Tetrahedron 61 2005 6726 6742
23. J.P. Marino, and J.C. Jaén J. Am. Chem. Soc. 104 1982 3165 3173
24. B.H. Lipshutz, D.A. Parker, J.A. Kozlowski, and S.L. Nguyen Tetrahedron Lett. 25 1984 5959 5962
25. A. Ghribi, A. Alexakis, and J.F. Normant Tetrahedron Lett. 25 1984 3075 3078
26. B.H. Lipshutz, R.S. Wilhelm, J.A. Kozlowski, and D.A. Parker J. Org. Chem. 49 1984 3928 3938
27. B.H. Lipshutz, J.A. Kozlowski, D.A. Parker, S.L. Nguyen, and K.E. McCarthy J. Organomet. Chem. 285 1985 437 447
28. A. Alexakis, D. Jachiet, and J.F. Normant Tetrahedron 42 1986 5607 5619
29. M.J. Eis, J.E. Wrobel, and B. Ganem J. Am. Chem. Soc. 106 1984 3693 3694
30. H.C. Brown, U.S. Racherla, and S.M. Singh Tetrahedron Lett. 25 1984 2411 2414
31. P. Crotti, V. Di Bussolo, L. Favero, M. Pineschi, and M. Pasero J. Org. Chem. 61 1996 9548 9552
32. T. Ooi, J. Morikawa, H. Ichikawa, and K. Maruoka Tetrahedron Lett. 40 1999 5881 5884
33. A. Alexakis, E. Vrancken, P. Mangeney, and F. Chemla J. Chem. Soc., Perkin Trans. 1 2000 3352 3353
34. H. Reich, A.W. Sanders, A.T. Fiedler, and M.J. Bevan J. Am. Chem. Soc. 124 2002 13386 13387
35. C. Schneider, and J. Brauner Tetrahedron Lett. 41 2000 3043 3046
36. C. Schneider, and J. Brauner Eur. J. Org. Chem. 2001 4445 4450
37. H. Zhou, E.J. Campbell, and S.T. Nguyen Org. Lett. 3 2001 2229 2231
38. H. Zhao, and B.L. Pagenkopf Chem. Commun. 2003 2592 2593
39. P. Restorp, and P. Somfai Eur. J. Org. Chem. 2005 3946 3951
40. M. Uchiyama, M. Kameda, O. Mishima, N. Yokoyama, M. Koike, Y. Kondo, and T. Sakamoto J. Am. Chem. Soc. 120 1998 4934 4946
41. E. Bellamy, O. Bayh, C. Hoarau, F. Trécourt, G. Quéguiner, and F. Marsais Chem. Commun. 2010 7043 7045
42. M. Mizuno, M. Kanai, A. Iida, and K. Tomioka Tetrahedron 53 1997 10699 10708
43. N. Oguni, Y. Miyagi, and K. Itoh Tetrahedron Lett. 39 1998 9023 9026
44. C. Zhu, M. Yang, J. Sun, Y. Zhu, and Y. Pan Synlett 2004 465 468
45. E. Vrancken, A. Alexakis, and P. Mangeney Eur. J. Org. Chem. 2005 1354 1366
46. S.K. Taylor, D.L. Clark, K.L. Heinz, S.B. Schramm, C.D. Westermann, and K.K. Barnell J. Org. Chem. 48 1983 592 596
47. M. Bandini, P.G. Cozzi, P. Melchiorre, and A. Umani-Ronchi J. Org. Chem. 67 2002 5386 5389
48. M. Bandini, P.G. Cozzi, P. Melchiorre, and A. Umani-Ronchi Angew. Chem., Int. Ed. 43 2004 84 97
49. M. Westermaier, and H. Mayr Chem. - Eur. J. 14 2008 1638 1647
50. F. Bertolini, P. Crotti, F. Macchia, and M. Pineschi Tetrahedron Lett. 47 2006 61 64
51. F. Bertolini, P. Crotti, V. Di Bussolo, F. Macchia, and M. Pineschi J. Org. Chem. 72 2007 7761 7764
52. For the ring-opening of styrene oxide by the nucleophilic attack of α-carbon atom of sodium β-naphtholate, see: C.O. Guss, and L.H. Jules J. Am. Chem. Soc. 72 1950 3878 3880
53. M. Schlosser Organometallics in Synthesis 1994 John-Wiley Sons
54. F. Chemla, and E. Vrancken Z. Rappaport, The Chemistry of Organolithium Compounds 2004 John Wiley & Sons 1165 1242
55. R. Chinchilla, C. Nájera, and M. Yus Chem. Rev. 104 2004 2667 2722
56. R.E. Mulvey, F. Mongin, M. Uchiyama, and Y. Kondo Angew. Chem., Int. Ed. 46 2007 3802 3824
57. R.E. Mulvey Acc. Chem. Res. 42 2009 743 755
58. B. Haag, M. Mosrin, H. Ila, V. Malakhov, and P. Knochel Angew. Chem., Int. Ed. 50 2011 9794 9824
59. P. Beak, and V. Snieckus Acc. Chem. Res. 15 1982 306 312
60. P. Beak, and A.I. Meyers Acc. Chem. Res. 19 1986 356 363
61. V. Snieckus Chem. Rev. 90 1990 879 933
62. D.B. Collum Acc. Chem. Res. 25 1992 448 454
63. M.C. Whisler, S. MacNeil, V. Snieckus, and P. Beak Angew. Chem., Int. Ed. 43 2004 2206 2225
64. D.W. Slocum, and C.A. Jennings J. Org. Chem. 41 1976 3653 3664
65. W. Bauer, and P.V.R. Schleyer J. Am. Chem. Soc. 111 1989 7191 7198
66. D.W. Slocum, D. Reed, F. Jackson III, and C. Friesen J. Organomet. Chem. 512 1996 265 267
67. M. Stratakis J. Org. Chem. 62 1997 3024 3025
68. R.A. Rennels, A.J. Maliakal, and D.B. Collum J. Am. Chem. Soc. 120 1998 421 422
69. D. Hoffmann, and D.B. Collum J. Am. Chem. Soc. 120 1998 5810 5811
70. S.T. Chadwick, R.A. Rennels, J.L. Rutherford, and D.B. Collum J. Am. Chem. Soc. 122 2000 8640 8647
71. D.W. Slocum, R. Moon, J. Thompson, D.S. Coffey, J.D. Li, M.G. Slocum, A. Siegel, and R. Gayton-Garcia Tetrahedron Lett. 35 1994 385 388
72. H. Gilman, and B.J. Gaj J. Org. Chem. 22 1957 1165 1168
73. S.C. Honeycutt J. Organomet. Chem. 29 1971 1 5
74. R.B. Bates, L.M. Kroposki, and D.E. Potter J. Org. Chem. 37 1972 560 562
75. A.J. Duggan, and F.E. Roberts Tetrahedron Lett. 20 1979 595 598
76. J. Clayden, and S.A. Yasin New J. Chem. 26 2002 191 192
77. S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunaga, K.B. Hansen, A.E. Gould, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 1307 1315
78. L.P.C. Nielsen, C.P. Stevenson, D.G. Blackmond, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 1360 1362
79. A. Berkessel, and E. Ertürk Adv. Synth. Catal. 348 2006 2619 2625
80. H. Pellisier Adv. Synth. Catal. 353 2011 1613 1666
81. H.J. Reich, D.P. Green, M.A. Medina, W.S. Goldenberg, B.Ö. Gudmundsson, R.R. Dykstra, and N.H. Phillips J. Am. Chem. Soc. 120 1998 7201 7210
82. W. Bauer, W.R. Winchester, and P.V.R. Schleyer Organometallics 6 1987 2371 2379
83. W. Bauer, P.A.A. Klusener, S. Harder, J.A. Kanters, A.J.M. Duisenberg, L. Brandsma, and P.V.R. Schleyer Organometallics 7 1988 552 555
84. H.J. Reich, W.H. Sikorski, B.Ö. Gudmundsson, and R.R. Dykstra J. Am. Chem. Soc. 120 1998 4035 4036
85. A. Boman, and D. Johnels Magn. Reson. Chem. 38 2000 853 860
86. H.J. Reich, W.S. Goldenberg, A.W. Sanders, and C.C. Tzschucke Org. Lett. 3 2001 33 36
87. H.J. Reich, W.S. Goldenberg, B.Ö. Gudmundsson, A.W. Sanders, K.J. Kulicke, K. Simon, and I.A. Guzei J. Am. Chem. Soc. 123 2001 8067 8079
88. A. Ramirez, X. Sun, and D.B. Collum J. Am. Chem. Soc. 128 2006 10326 10336
89. R.A. Gossage, J.T.B.H. Jastrzebski, and G.V. Koten Angew. Chem., Int. Ed. 44 2005 1448 1454
90. T.F. Briggs, M.D. Winemiller, D.B. Collum, R.L. Parsons, A.H. Davulcu, G.D. Harris, J.M. Fortunak, and P.N. Confalone J. Am. Chem. Soc. 126 2004 5427 5435
91. S. Harder, J. Boersma, L. Brandsma, G.P.M.V. Mier, and J.A. Kanters J. Organomet. Chem. 364 1989 1 15
92. R.R. Fraser, and T.S. Mansour Tetrahedron Lett. 27 1986 331 334
93. R. Brückner Chem. Ber. 122 1989 703 710
94. A.J. Vázquez, and N.S. Nudelman ARKIVOC xii 2005 332 340
95. M.V. Bhatt, and S.U. Kulkarni Synthesis 1983 249 282
96. S.A. Weissman, and D. Zewge Tetrahedron 61 2005 7833 7863
97. N. Di Blasio, M.T. Lopardo, and P. Lupattelli Eur. J. Org. Chem. 2009 938 944