Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines via enantioselective transmetalation

Journal of the American Chemical Society

Volumn 134, Issue 41, 2012, Pages 16955-16958

  Shintani, Ryo ^a   MacIver, Eleanor E ^a   Tamakuni, Fumiko ^a   Hayashi, Tamio ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b INSTITUTE OF MATERIALS RESEARCH AND ENGINEERING   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; RHODIUM-CATALYZED; TRANSMETALATION;

CATALYSIS; RHODIUM;

ENANTIOSELECTIVITY;

DIBENZOOXASILINE DERIVATIVE; LIGAND; RHODIUM; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOSELECTIVE TRANSMETALATION; ENANTIOSELECTIVITY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM; SILICON; SILICON COMPOUNDS; STEREOISOMERISM;

EID: 84867518040     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3076555     Document Type: Article

References (52)

1. Chem. Soc. Rev. 2011, 40, 4877-5208 (Beller, M., Ed.; themed issue for cross-coupling reactions in organic synthesis).
2. J. Organomet. Chem. 2002, 653, 1-133 (Tamao, K., Hiyama, T., Negishi, E., Eds.; special issue for cross-coupling).
3. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: Hoboken, NJ, 2002.
4. Berthon-Gelloz, G.; Hayashi, T. In Boronic Acids, 2 nd ed.; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2011; p 263.
5. Edwards, H. J.; Hargrave, J. D.; Penrose, S. D.; Frost, C. G. Chem. Soc. Rev. 2010, 39, 2093
6. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129
7. Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793
8. Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973
9. Boudier, A.; Knochel, P. Tetrahedron Lett. 1999, 40, 687
10. Hölzer, B.; Hoffmann, R. W. Chem. Commun. 2003, 732
11. Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024
12. Awano, T.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 20738 and the references cited therein
13. Desymmetrization of diaryl sulfoxides by stoichiometric asymmetric sulfoxide-magnesium exchange has been reported: Hampel, T.; Ruppenthal, S.; Sälinger, D.; Brückner, R. Chem.-Eur. J. 2012, 18, 3136
14. Xu, L.-W.; Li, L.; Lai, G.-Q.; Jiang, J.-X. Chem. Soc. Rev. 2011, 40, 1777
15. Oestreich, M. Synlett 2007, 1629
16. Rendler, S.; Auer, G.; Oestreich, M. Angew. Chem., Int. Ed. 2005, 44, 7620
17. Rendler, S.; Auer, G.; Keller, M.; Oestreich, M. Adv. Synth. Catal. 2006, 348, 1171
18. Rendler, S.; Oestreich, M.; Butts, C. P.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 2007, 129, 502
19. Klare, H. F. T.; Oestreich, M. Angew. Chem., Int. Ed. 2007, 46, 9335
20. Hayashi, T.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1974, 15, 331
21. Corriu, R. J. P.; Moreau, J. J. E. J. Organomet. Chem. 1975, 85, 19
22. Ohta, T.; Ito, M.; Tsuneto, A.; Takaya, H. J. Chem. Soc., Chem. Commun. 1994, 2525
23. Corriu, R. J. P.; Moreau, J. J. E. Tetrahedron Lett. 1973, 14, 4469
24. Corriu, R. J. P.; Moreau, J. J. E. J. Organomet. Chem. 1976, 120, 337
25. Yasutomi, Y.; Suematsu, H.; Katsuki, T. J. Am. Chem. Soc. 2010, 132, 4510
26. Shintani, R.; Moriya, K.; Hayashi, T. J. Am. Chem. Soc. 2011, 133, 16440
27. Shintani, R.; Moriya, K.; Hayashi, T. Org. Lett. 2012, 14, 2902
28. Shintani, R.; Otomo, H.; Ota, K.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 7305
29. Tamao, K.; Nakamura, K.; Ishii, H.; Yamaguchi, S.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 12469
30. Schmidt, D. R.; O'Malley, S. J.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 1190
31. Igawa, K.; Takada, J.; Shimono, T.; Tomooka, K. J. Am. Chem. Soc. 2008, 130, 16132
32. Nakao, Y.; Imanaka, H.; Sahoo, A. K.; Yada, A.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 6952
33. Nakao, Y.; Chen, J.; Tanaka, M.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 11694
34. Nakao, Y.; Takeda, M.; Matsumoto, T.; Hiyama, T. Angew. Chem., Int. Ed. 2010, 49, 4447
35. Nakao, Y.; Chen, J.; Imanaka, H.; Hiyama, T.; Ichikawa, Y.; Duan, W.-L.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 9137
36. Shintani, R.; Ichikawa, Y.; Hayashi, T.; Chen, J.; Nakao, Y.; Hiyama, T. Org. Lett. 2007, 9, 4643
37. Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2009, 131, 10844
38. Krasnova, T. L.; Chernyshev, E. A.; Sergeev, A. P.; Abramova, E. S. Russ. Chem. Bull. 1997, 46, 1487
39. Kirillova, N. I.; Cusev, A. I.; Sharapov, V. A.; Afanasova, O. B.; Zubarev, Y. E.; Alekseev, N. V.; Chernyshev, E. A.; Struchkov, Y. T. J. Organomet. Chem. 1986, 306, 55 and the references cited therein
40. Werner, H.; Bosch, M.; Schneider, M. E.; Hahn, C.; Kukla, F.; Manger, M.; Windmüller, B.; Weberndörfer, B.; Laubender, M. J. Chem. Soc., Dalton Trans. 1998, 3549
41. Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2011, 50, 11098
42. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518
43. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125
44. CCDC-893230 and CCDC-893231 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. See also the Supporting Information for details.
45. Sommer, L. H.; Rodewald, P. G.; Parker, G. A. Tetrahedron Lett. 1962, 821
46. Corriu, R. J. P.; Lanneau, G. F.; Leard, M. J. Organomet. Chem. 1974, 64, 79
47. Corriu, R. J. P.; Guerin, C. J. Organomet. Chem. 1980, 198, 231
48. Zou, G.; Wang, Z.; Zhu, J.; Tang, J. Chem. Commun. 2003, 2438
49. Lautens, M.; Mancuso, J.; Grover, H. Synthesis 2004, 2006
50. Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358
51. de la Herrán, G.; Murcia, C.; Csákÿ, A. G. Org. Lett. 2005, 7, 5629
52. Kurahashi, T.; Shinokubo, H.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 6336