Addition of TMS-substituted oxiranyl anions to acylsilanes. A highly stereoselective approach to tetrasubstituted (Z)-β-hydroxy-α-TMS silyl enol ethers

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1440-1443

  Song, Zhenlei ^a,b   Kui, Leizhou ^a   Sun, Xianwei ^a   Li, Linjie ^a  

^a SICHUAN UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ETHER DERIVATIVE; SILANE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; COMBINATORIAL CHEMISTRY TECHNIQUES; ETHERS; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM; TRIMETHYLSILYL COMPOUNDS;

EID: 79952590878     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200116f     Document Type: Article

References (75)

1. For reviews, see: Brownbridge, P. Synthesis 1983, 1
2. Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181
3. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063
4. Kobayashi, S.; Manabe, K.; Ishitani, H.; Matsuo, J.-I. Sci. Synth. 2002, 4, 317
5. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066
6. Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495
7. Hall, P. L.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571
8. Smietana, M.; Mioskowski, C. Org. Lett. 2001, 3, 1037
9. Aggarwal, V. K.; Sheldon, C. G.; MacDonald, G. J.; Martin, W. P. J. Am. Chem. Soc. 2002, 124, 10300
10. Denmark, S. E.; Pham, S. M. J. Org. Chem. 2003, 68, 5045
11. Ooguri, A.; Ikeda, Z.; Matsubara, S. Chem. Commun. 2007, 4761
12. Davis, F. A.; Sheppard, A. C.; Chen, B. C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679
13. Morikawa, K.; Park, J.; Andersson, P. G.; Hashiyama, T.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 8463
14. Ishii, A.; Kojima, J.; Mikami, K. Org. Lett. 1999, 1, 2013
15. Cahard, D.; Audouard, C.; Plaquevent, J. C.; Roques, N. Org. Lett. 2000, 2, 3699
16. Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375
17. Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379
18. Zhang, Y.-H.; Shibatomi, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 15038
19. Cardinal, D. B.; Guerin, B.; Guindon, Y. J. Org. Chem. 2005, 70, 776
20. Fujisawa, H.; Takahashi, E.; Mukaiyama, T. Chem.-Eur. J. 2006, 12, 5082
21. Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2764
22. Kokubo, M.; Ogawa, C.; Kobayashi, S. Angew. Chem., Int. Ed. 2008, 47, 6909
23. Mikami, K.; Kawakami, Y.; Akiyama, K.; Aikawa, K. J. Am. Chem. Soc. 2007, 129, 12950
24. Clift, M. D.; Taylor, C. N.; Thomson, R. J. Org. Lett. 2007, 9, 4667
25. Ishii, A.; Kojima, J.; Mikami, K. Org. Lett. 1999, 1, 2013
26. Ho, C. Y.; Ohmiya, H.; Jamison, T. F. Angew. Chem., Int. Ed. 2008, 47, 1893
27. Tsubouchi, A.; Enatsu, S.; Kanno, R.; Takeda, T. Angew. Chem., Int. Ed. 2010, 49, 7089
28. Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1976, 98, 4646
29. Eisch, J. J.; Galle, J. E. J. Organomet. Chem. 1988, 341, 293
30. Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042
31. Marie, J. C.; Courillon, C.; Malacria, M. Synlett 2002, 4, 553
32. Courillon, C.; Marie, J. C.; Malacria, M. Tetrahedron 2003, 59, 9759
33. Marie, J. C.; Courillon, C.; Malacria, M. Eur. J. Org. Chem. 2006, 2, 463
34. Nagaki, A.; Takizawa, E.; Yoshida, J. I. Chem. Lett. 2009, 38, 486 For reviews on oxiranyl anions, see: Satoh, T. Chem. Rev. 1996, 96, 3303
35. Hodgson, D. M.; Gras, E. Synthesis 2002, 1625
36. For the latest review, see: Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7 For recent representative studies on acylsilanes, see: Li, F. Q.; Zhong, S.; Lu, G.; Chan, A. S. C. Adv. Synth. Catal. 2009, 351, 1955
37. Tarr, J. C.; Johnson, J. S. Org. Lett. 2009, 11, 3870
38. Lettan, R. B.; Galliford, C. V.; Woodward, C. C.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 8805
39. Greszler, S. N.; Johnson, J. S. Angew. Chem., Int. Ed. 2009, 48, 3689
40. Shen, Z. M.; Dong, V. M. Angew. Chem., Int. Ed. 2009, 48, 748
41. Yoshikawa, T.; Mori, S.; Shindo, M. J. Am. Chem. Soc. 2009, 131, 2092
42. Greszler, S. N.; Johnson, J. S. Org. Lett. 2009, 11, 827
43. Unger, R.; Weisser, F.; Chinkov, N.; Stanger, A.; Cohen, T.; Marek, I. Org. Lett. 2009, 11, 1853
44. Sasaki, M.; Oyamada, K.; Takeda, K. J. Org. Chem. 2010, 75, 3941
45. Tarr, J. C.; Johnson, J. S. J. Org. Chem. 2010, 75, 3317
46. Smith, A. G.; Johnson, J. S. Org. Lett. 2010, 12, 1784
47. Schmitt, D. C.; Johnson, J. S. Org. Lett. 2010, 12, 944
48. Matsuo, J.-i.; Hattori, Y.; Ishibashi, H. Org. Lett. 2010, 12, 2294
49. Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225
50. Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423
51. Kato, M.; Mori, A.; Oshino, H.; Enda, J.; Kobayashi, K.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 1773
52. Enda, J.; Kuwajima, I. J. Am. Chem. Soc. 1985, 107, 5495
53. For reviews, see: Brook, A. G. Acc. Chem. Res. 1974, 7, 77
54. Moser, W. H. Tetrahedron 2001, 57, 2065
55. Clayden, J.; Watsona, D. W.; Chambers, M. Tetrahedron 2005, 61, 3195
56. Robertson, B. D.; Hartel, A. M. Tetrahedron Lett. 2008, 49, 2088
57. Baker, H. K.; Hartel, A. M. Tetrahedron Lett. 2009, 50, 4012
58. For studies on 1,2- vs 1,3-silyl migration, see: Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791
59. Taguchi, H.; Ghoroku, K.; Tadaki, M.; Tsubouchi, A.; Takeda, T. J. Org. Chem. 2002, 67, 8450
60. Xin, L. H.; David, A. N.; Johnson, J. S. Org. Lett. 2002, 4, 2957
61. sp2 to O silyl migration, see: Moser, W. H.; Endsley, K. E.; Colyer, J. T. Org. Lett. 2000, 2, 718
62. Taguchi, H.; Ghoroku, K.; Tadaki, M.; Tsubouchi, A.; Takeda, T. Org. Lett. 2001, 3, 3811
63. Moser, W. H.; Zhang, J.; Lecher, C. S.; Frazier, T. L.; Pink, M. Org. Lett. 2002, 4, 1981
64. Tsubouchi, A.; Itoh, M.; Onishi, K.; Takeda, T. Synthesis 2004, 9, 1504
65. Taguchi, H.; Takami, K.; Tsubouchi, A.; Takeda, T. Tetrahedron Lett. 2004, 45, 429
66. Devarie-Baez, N. O.; Shuhler, B. J.; Wang, H.; Xian, M. Org. Lett. 2007, 9, 4655
67. Smith, A. B., III; Kim, W. S.; Wuest, W. M. Angew. Chem., Int. Ed. 2008, 47, 7082
68. Devarie-Baez, N. O.; Kim, W. S.; Smith, A. B., III; Xian, M. Org. Lett. 2009, 11, 1861
69. Smith, A. B., III; Kim, W. S.; Tong, R. B. Org. Lett. 2010, 12, 588
70. Tsubouchi, A.; Kira, T.; Takeda, T. Synlett 2006, 2577
71. Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867
72. Burford, C.; Cooke, F.; Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1977, 99, 4536
73. 5, in which only the reduced product of acylsilane 1j was obtained via a proposed successive SET process.
74. The authors thank referees' helpful suggestions on proposing this mechanism. In addition, despite formation of the corresponding β-silyloxy ketone being possible for the E -isomer via O to O silyl transfer, no such compounds were observed after isolation.
75. The stereochemistry of 9 was determined by NOE experiments of α-bromo enone 10, which was obtained in 79% yield through a Peterson olefination protocol of 9 with NaH in DMF.