Stereoconvergent [1,2]- and [1,4]-wittig rearrangements of 2-silyl-6-aryl-5,6-dihydropyrans: A tale of steric Vs electronic regiocontrol of divergent pathways

Journal of Organic Chemistry

Volumn 80, Issue 2, 2015, Pages 1163-1191

  Mori Quiroz, Luis M ^a   Maleczka, Robert E ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS;

AROMATIC MOIETIES; DIASTEREO-SELECTIVITY; DIASTEREOMERIC; DIASTEREOMERS; DIRECTING GROUPS; RING CONTRACTION; STERICALLY DEMANDING; WITTIG REARRANGEMENT;

AROMATIC COMPOUNDS;

2 SILYL 6 ARYL 5,6 DIHYDRO (2H) PYRAN DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG; SILANE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DIASTEREOISOMER; EPIMERIZATION; ISOMERIZATION; REACTION TIME; RING CLOSING METATHESIS; STEREOCHEMISTRY; SUZUKI REACTION; WITTIG REARRANGEMENT; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; MOLECULAR STRUCTURE; PYRANS; SILANES; STEREOISOMERISM;

EID: 84921369628     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5026942     Document Type: Article

References (80)

1. Wittig, G.; Lohmann, L. Justus Liebigs Ann. Chem. 1942, 550, 260-268
2. Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885-902
3. Nakai, T.; Tomooka, K. Pure Appl. Chem. 1997, 69, 595-600
4. Tomooka, K.; Yamamoto, H.; Nakai, T. Liebigs Ann./Recl. 1997, 1275-1281
5. Felkin, H.; Tambute, A. Tetrahedron Lett. 1969, 821-822
6. Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1970, 9, 763-773
7. Briére, R.; Chérest, M.; Felkin, H.; Frajerman, C. Tetrahedron Lett. 1977, 18, 3489-3492
8. Rautenstrauch, V. Helv. Chim. Acta 1972, 55, 594-609
9. Schlosser, M.; Strunk, S. Tetrahedron 1989, 45, 2649-2664
10. Felkin, H.; Frajerman, C. Tetrahedron Lett. 1977, 18, 3485-3488
11. Tomooka, K.; Yamamoto, H.; Nakai, T. Angew. Chem., Int. Ed. 2000, 39, 4500-4502
12. Hodgson, D. M.; Tomooka, K.; Gras, E. Top. Organomet. Chem. 2003, 5, 217-250
13. Onyeozili, E. N.; Maleczka, R. E. Chem. Commun. 2006, 2466-2468
14. Onyeozili, E. N.; Mori-Quiroz, L. M.; Maleczka, R. E. Tetrahedron 2013, 69, 849-860
15. Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925-2931
16. Marshall, J. A.; Robinson, E. D.; Lebreton, J. J. Org. Chem. 1990, 55, 227-239
17. Marshall, J. A.; Wallace, E. M.; Coan, P. S. J. Org. Chem. 1995, 60, 796-797
18. Takahashi, T.; Nemoto, H.; Kanda, Y.; Tsuji, J.; Fujise, Y. J. Org. Chem. 1986, 51, 4315-4316
19. Takahashi, T.; Nemoto, H.; Kanda, Y.; Tsuji, J.; Fukazawa, Y.; Okajima, T.; Fujise, Y. Tetrahedron 1987, 43, 5499-5520
20. Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465-3467
21. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469-1502
22. Tsubuki, M.; Takahashi, K.; Honda, T. J. Org. Chem. 2003, 68, 10183-10186
23. Mazaleyrat, J. P.; Welvart, Z. Nouv. J. Chim. 1983, 7, 491-497
24. Schmidt, R. R.; Beitzke, B. Chem. Ber. 1983, 116, 2115-2135
25. Verner, E. J.; Cohen, T. J. Org. Chem. 1992, 57, 1072-1073
26. Verner, E. J.; Cohen, T. J. Am. Chem. Soc. 1992, 114, 375-377
27. Soloshonok, V. A.; Ohkura, H.; Yasumoto, M. J. Fluorine Chem. 2006, 127, 708-711
28. Biellmann, J.-F.; Ducep, J. B. Tetrahedron Lett. 1970, 2899-2902
29. Biellmann, J.-F.; Ducep, J. B.; Vicens, J. J. Tetrahedron 1976, 32, 1801-1805
30. Reglier, M.; Julia, S. A. Tetrahedron Lett. 1983, 24, 2387-2390
31. Reglier, M.; Julia, S. A. Tetrahedron Lett. 1985, 26, 2319-2322
32. Larsen, S. D. J. Am. Chem. Soc. 1988, 110, 5932-5934
33. Larsen, S. D.; Fisher, P. V.; Libby, B. E.; Jensen, R. M.; Mizsak, S. A.; Watt, W.; Ronk, W. R.; Hill, S. T. J. Org. Chem. 1996, 61, 4725-4738
34. Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, 5322-5324
35. Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256-4264
36. Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050
37. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935
38. Maas, G. Chem. Soc. Rev. 2004, 33, 183-190
39. Lin, W.; Charette, A. B. Adv. Synth. Catal. 2005, 347, 1547-1552
40. Thompson, J. L.; Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 6090-6091
41. Chuprakov, S.; Kwok, S. W.; Zhang, L.; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034-18035
42. Bull, J. A.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 1895-1902
43. Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. Q. J. Am. Chem. Soc. 2001, 123, 2964-2969
44. Risatti, C. A.; Taylor, R. E. Angew. Chem., Int. Ed. 2004, 43, 6671-6672
45. Hodgson, D. M.; Chung, Y. K.; Nuzzo, I.; Freixas, G.; Kulikiewicz, K. K.; Cleator, E.; Paris, J. M. J. Am. Chem. Soc. 2007, 129, 4456-4462
46. You, B.; Hamer, K.; Lewis, W.; Dowden, J. Chem. Commun. 2013, 49, 795-797
47. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382
48. Aubert, C.; Fensterbank, L.; Garcia, P.; Malacria, M.; Simonneau, A. Chem. Rev. 2011, 111, 1954-1993
49. Watson, I. D. G.; Toste, F. D. Chem. Sci. 2012, 3, 2899-2919
50. Haven, T.; Kubik, G.; Haubenreisser, S.; Niggemann, M. Angew. Chem., Int. Ed. 2013, 52, 4016-4019
51. Moyano, A.; Rios, R. Chem. Rev. 2011, 111, 4703-4832
52. Onyeozili, E. N.; Maleczka, R. E. Tetrahedron Lett. 2006, 47, 6565-6568
53. Hayakawa, K.; Hayashida, A.; Kanematsu, K. J. Chem. Soc., Chem. Commun. 1988, 1108-1110
54. Mikami, K.; Kishi, N.; Nakai, T. Chem. Lett. 1989, 1683-1686
55. Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1115-1118
56. Sun, X. W.; Lei, J.; Sun, C. Z.; Song, Z. L.; Yan, L. J. Org. Lett. 2012, 14, 1094-1097
57. Dust, J. M.; Arnold, D. R. J. Am. Chem. Soc. 1983, 105, 1221-1227
58. Greatrex, B. W.; Taylor, D. K.; Tiekink, E. R. T. Org. Lett. 2002, 4, 221-224
59. Eliel, E. L.; Manoharan, M. J. Org. Chem. 1981, 46, 1959-1962
60. Kitching, W.; Olszowy, H. A.; Drew, G. M.; Adcock, W. J. Org. Chem. 1982, 47, 5153-5156
61. Meyers, A. I.; Campbell, A. L.; Abatjoglou, A. G.; Eliel, E. L. Tetrahedron Lett. 1979, 4159-4162
62. Ragot, J. P.; Prime, M. E.; Archibald, S. J.; Taylor, R. J. K. Org. Lett. 2000, 2, 1613-1616
63. Lehn, J. M.; Wipff, G. J. Am. Chem. Soc. 1976, 98, 7498-7505
64. Cuevas, G.; Juaristi, E. J. Am. Chem. Soc. 1997, 119, 7545-7549
65. Cohen, T.; Lin, M. T. J. Am. Chem. Soc. 1984, 106, 1130-1131
66. Rychnovsky, S. D. J. Org. Chem. 1989, 54, 4982-4984
67. Rychnovsky, S. D.; Mickus, D. E. Tetrahedron Lett. 1989, 30, 3011-3014
68. Jernigan, M. T.; Eliel, E. L. J. Am. Chem. Soc. 1995, 117, 9638-9644
69. Rychnovsky, S. D.; Buckmelter, A. J.; Dahanukar, V. H.; Skalitzky, D. J. J. Org. Chem. 1999, 64, 6849-6860
70. Fraenkel, G.; Chow, A.; Fleischer, R.; Liu, H. J. Am. Chem. Soc. 2004, 126, 3983-3995
71. Fraenkel, G.; Gallucci, J.; Liu, H. J. Am. Chem. Soc. 2006, 128, 8211-8216
72. Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y. M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393-5396
73. Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. M. J. Org. Chem. 1991, 56, 7076-7083
74. Leonard, N. M.; Woerpel, K. A. J. Org. Chem. 2009, 74, 6915-6923
75. Curran, D. P.; Gothe, S. A. Tetrahedron 1988, 44, 3945-3952
76. An, I.; Onyeozili, E. N.; Maleczka, R. E. Tetrahedron: Asymmetry 2010, 21, 527-534
77. Abdallah, H.; Gree, R.; Carrie, R. Tetrahedron Lett. 1982, 23, 503-506
78. Arai, I.; Mori, A.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 8254-8256
79. Schmittel, M.; Mahajan, A. A.; Bucher, G.; Bats, J. W. J. Org. Chem. 2007, 72, 2166-2173
80. Pelletier, G.; Bechara, W. S.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 12817-12819