Palladium-catalyzed enantioselective desymmetrization of silacyclobutanes: Construction of silacycles possessing a tetraorganosilicon stereocenter

Journal of the American Chemical Society

Volumn 133, Issue 41, 2011, Pages 16440-16443

  Shintani, Ryo ^a   Moriya, Kohei ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL PHOSPHORAMIDITE LIGANDS; DESYM-METRIZATION; ENANTIOSELECTIVE; STEREOCENTERS;

ACETYLENE; ENANTIOSELECTIVITY;

CATALYSIS;

BUTANE; LIGAND; ORGANOSILICON DERIVATIVE; PALLADIUM; PHOSPHORAMIDOUS ACID; SILACYCLOBUTANE; TETRAORGANOSILICON; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; SYNTHESIS;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOSILICON COMPOUNDS; PALLADIUM; SILANES; STEREOISOMERISM;

EID: 80054727634     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja208621x     Document Type: Article

References (59)

1. Phosphorus Ligands in Asymmetric Catalysis 1-3; Börner, A., Ed.; Wiley-VCH: Weinheim, Germany, 2008.
2. New Frontiers in Asymmetric Catalysis; Mikami, K., Lautens, M., Eds.; Wiley: Hoboken, NJ, 2007.
3. Catalytic Asymmetric Synthesis, 2 nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
4. Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999.
5. Xu, L.-W.; Li, L.; Lai, G.-Q.; Jiang, J.-X. Chem. Soc. Rev. 2011, 40, 1777
6. Oestreich, M. Synlett 2007, 1629
7. Sommer, L. H. Stereochemistry, Mechanism and Silicon: An Introduction to the Dynamic Stereochemistry and Reaction Mechanisms of Silicon Centers; McGraw-Hill: New York, 1965.
8. Strohmann, C.; Hörnig, J.; Auer, D. Chem. Commun. 2002, 766
9. Trzoss, M.; Shao, J.; Bienz, S. Tetrahedron: Asymmetry 2004, 15, 1501
10. Rendler, S.; Auer, G.; Oestreich, M. Angew. Chem., Int. Ed. 2005, 44, 7620
11. Rendler, S.; Auer, G.; Keller, M.; Oestreich, M. Adv. Synth. Catal. 2006, 348, 1171
12. Rendler, S.; Oestreich, M.; Butts, C. P.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 2007, 129, 502
13. Igawa, K.; Takada, J.; Shimono, T.; Tomooka, K. J. Am. Chem. Soc. 2008, 130, 16132 (this paper includes one catalytic example)
14. Igawa, K.; Kokan, N.; Tomooka, K. Angew. Chem., Int. Ed. 2010, 49, 728
15. Ottosson, H.; Eklöf, A. M. Coord. Chem. Rev. 2008, 252, 1287
16. Hayashi, T.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1974, 15, 331
17. Corriu, R. J. P.; Moreau, J. J. E. J. Organomet. Chem. 1975, 85, 19
18. Ohta, T.; Ito, M.; Tsuneto, A.; Takaya, H. J. Chem. Soc., Chem. Commun. 1994, 2525
19. Corriu, R. J. P.; Moreau, J. J. E. Tetrahedron Lett. 1973, 14, 4469
20. Corriu, R. J. P.; Moreau, J. J. E. J. Organomet. Chem. 1976, 120, 337
21. Schmidt, D. R.; OMalley, S. J.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 1190
22. Tamao, K.; Nakamura, K.; Ishii, H.; Yamaguchi, S.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 12469
23. Yasutomi, Y.; Suematsu, H.; Katsuki, T. J. Am. Chem. Soc. 2010, 132, 4510
24. Sakurai, H.; Imai, T. Chem. Lett. 1975, 891
25. Takeyama, Y.; Nozaki, K.; Matsumoto, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1461
26. Tanaka, Y.; Yamashita, H.; Tanaka, M. Organometallics 1996, 15, 1524
27. Chauhan, B. P. S.; Tanaka, Y.; Yamashita, H.; Tanaka, M. Chem. Commun. 1996, 1207
28. Tanaka, Y.; Nishigaki, A.; Kimura, Y.; Yamashita, M. Appl. Organomet. Chem. 2001, 15, 667
29. Tanaka, Y.; Yamashita, M. Appl. Organomet. Chem. 2002, 16, 51
30. Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2006, 8, 483
31. Hirano, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 6094
32. Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 10, 2199
33. Weyenberg, D. R.; Nelson, L. E. J. Org. Chem. 1965, 30, 2618
34. Hatanaka, Y.; Watanabe, M.; Onozawa, S.; Tanaka, M.; Sakurai, H. J. Org. Chem. 1998, 63, 422
35. Saso, H.; Ando, W. Chem. Lett. 1988, 17, 1567
36. Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821
37. Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495
38. Denmark, S. E.; Wang, Z. Synthesis 2000, 999
39. Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620
40. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346
41. Arnold, L. A.; Imbos, R.; Mandolin, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865
42. Agenet, N.; Mirebeau, J.-H.; Petit, M.; Thouvenot, R.; Gandon, V.; Malacria, M.; Aubert, C. Organometallics 2007, 26, 819
43. Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184
44. Pelz, N. F.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328
45. Kündig, E. P.; Chaudhuri, P. D.; House, D.; Bernardinelli, G. Angew. Chem., Int. Ed. 2006, 45, 1092
46. Trost, B. M.; Stambuli, J. P.; Silverman, S. M.; Schwörer, U. J. Am. Chem. Soc. 2006, 128, 13328
47. Trost, B. M.; Silverman, S. M.; Stambuli, J. P. J. Am. Chem. Soc. 2007, 129, 12398
48. Trost, B. M.; Silverman, S. M. J. Am. Chem. Soc. 2010, 132, 8238
49. Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 11688
50. Shintani, R.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 12356
51. Shintani, R.; Park, S.; Shirozu, F.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 16174
52. Albicker, M. R.; Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 9139
53. Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79
54. Watanabe, T.; Knöpfel, T. F.; Carreira, E. M. Org. Lett. 2003, 5, 4557
55. Shintani, R.; Park, S.; Duan, W.-L.; Hayashi, T. Angew. Chem., Int. Ed. 2007, 46, 5901
56. Aggarwal, V. K.; Binanzer, M.; de Ceglie, M. C.; Gallanti, M.; Glasspoole, B. W.; Kendrick, S. J. F.; Sonawane, R. P.; Vázquez-Romero, A.; Webster, M. P. Org. Lett. 2011, 13, 1490
57. Tanaka, Y.; Yamashita, H.; Shimada, S.; Tanaka, M. Organometallics 1997, 16, 3246
58. Wolkowski, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4289
59. Mann, G.; Shelby, Q.; Roy, A. H.; Hartwig, J. F. Organometallics 2003, 22, 2775