Copper-catalyzed highly enantioselective carbenoid insertion into Si-H bonds

Angewandte Chemie - International Edition

Volumn 47, Issue 44, 2008, Pages 8496-8498

  Zhang, Yong Zhen ^a   Zhu, Shou Fei ^a   Wang, Li Xin ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Carbenoids; Copper; Insertion; N ligands

Indexed keywords

CHEMICAL REACTIONS; COPPER; ORGANIC COMPOUNDS; SILANES; SILICON;

ASYMMETRIC CATALYSIS; CARBENOID INSERTIONS; CARBENOIDS; CATALYTIC SYSTEMS; CHEMICAL EQUATIONS; COMPLETE CONTROLS; DIIMINE; ENANTIOCONTROL; ENANTIOMERIC EXCESSES; ENANTIOSELECTIVE; H BONDS; HIGH YIELDS; HIGHLY EFFICIENT; INSERTION; N LIGANDS; TRIFLUOROMETHANESULFONATE;

LIGANDS;

CARBENE; COPPER; DRUG DERIVATIVE; HYDROGEN; METHANE; SILANE DERIVATIVE; SILICON;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COPPER; HYDROGEN; METHANE; SILANES; SILICON; STEREOISOMERISM;

EID: 54249162850     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803192     Document Type: Article

References (26)

1. I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
2. For reviews, see: a) M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998;
3. b) M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911.
4. For earlier examples of copper-catalyzed carbenoid insertions into Si-H bonds, see: a) F. Rijkens, M. J. Janssen, W. Drenth, G. J. M. van derKerk, J. Organomet. Chem. 1964, 2, 347;
5. b) H. Watanabe, T. Nakano, K.-I. Araki, H. Matsumoto, Y. J. Nagai, J. Organomet. Chem. 1974, 69, 389;
6. c) V. E. Baikov, L. P. Danilkina, K. A. Oglobin, J. Gen. Chem. 1981, 51, 1858.
7. For earlier examples of rhodium-catalyzed carbenoid insertions into Si-H bonds, see: d) V. Bagheri, M. P. Doyle, J. Taunton, E. E. Claxton, J. Org. Chem. 1988, 53, 6158;
8. e) O. Andrey, Y. Landai, D. Planchenault, Tetrahedron Lett. 1993, 34, 2977;
9. f) Y. Landais, D. Planchenault, Tetrahedron Lett. 1994, 35, 9549;
10. g) O. Andrey, Y. Landais, D. Planchenault, V. Weber, Tetrahedron 1995, 51, 12083.
11. R. T. Buck, M. P. Doyle, M. J. Drysdale, L. Ferris, D. C. Forbes, D. Haigh, C. J. Moody, N. D. Pearson, Q.-L. Zhou, Tetrahedron Lett. 1996, 37, 7631.
12. H. M. L. Davies, T. Hansen, J. Rutberg, P. R. Bruzinski, Tetrahedron Lett. 1997, 38, 1741.
13. M. Ge, E. J. Corey, Tetrahedron Lett. 2006, 47, 2319.
14. a) P. Bulugahapitiya, Y. Landais, L. Parra-Rapado, D. Planchenault, V. Weber, J. Org. Chem. 1997, 62, 1630;
15. b) R. T. Buck, D. M. Coe, M. J. Drysdale, C. J. Moody, N. D. Pearson, Tetrahedron Lett. 1998, 39, 7181;
16. c) S. Kitagaki, M. Kinoshita, M. Takeba, M. Anada, S. Hashimoto, Tetrahedron: Asymmetry 2000, 11, 3855;
17. d) R. T. Buck, D. M. Coe, M. J. Drysdale, L. Ferris, D. Haigh, C. J. Moody, N. D. Pearson, J. B. Sanghera, Tetrahedron: Asymmetry 2003, 14, 791.
18. For examples of diastereoselective Si-H bond insertion, see: e) Y. Landais, D. Planchenault, Tetrahedron Lett. 1994, 35, 4565;
19. f) Y. Landais, D. Planchenault, V. Weber, Tetrahedron Lett. 1994, 35, 9549.
20. a) L. A. Dakin, S. E. Schaus, E. N. Jacobsen, J. S. Panek, Tetrahedron Lett. 1998, 39, 8947;
21. b) L. A. Dakin, P. C. Ong, J. S. Panek, R. J. Staples, P. Stavropoulos, Organometallics 2000, 19, 2896.
22. B. Liu, S.-F. Zhu, W. Zhang, C. Chen, Q.-L. Zhou, J. Am. Chem. Soc. 2007, 129, 5834.
23. a) C. Chen, S.-F. Zhu, B. Liu, L.-X. Wang, Q.-L. Zhou, J. Am. Chem. Soc. 2007, 129, 12616;
24. b) S.-F. Zhu, C. Chen, Y. Cai, O.-L. Zhou, Angew. Chem. 2008, 120, 946;
25. Angew. Chem. Int. Ed. 2008, 47, 932.
26. C. Chen, S.-F. Zhu, X.-Y. Wu, Q.-L. Zhou, Tetrahedron: Asymmetry 2006, 17, 2761.