A modular assembly of chiral oxazolinylcarbene-rhodium complexes: Efficient phosphane-free catalysts for the asymmetric hydrosilylation of dialkyl ketones

Angewandte Chemie - International Edition

Volumn 43, Issue 8, 2004, Pages 1014-1017

  Gade, Lutz H ^a,b   César, Vincent ^a   Bellemin Laponnaz, Stéphane ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Asymmetric catalysis; Carbene ligands; Hydrosilylation; Ketones; Rhodium

Indexed keywords

CATALYSIS; COMPLEXATION; KETONES; PROBLEM SOLVING;

CHIRALS; HYDROSILYLATION; LIGANDS; MOIETY;

RHODIUM COMPOUNDS;

CARBENOID; KETONE DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMBINATORIAL CHEMISTRY; ENANTIOSELECTIVITY; HYDROSILYLATION; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 4143134810     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353133     Document Type: Article

References (44)

1. a) G. Helmchem, A. Pfaltz, Acc. Chem. Res. 2000, 33, 326;
2. b) for a general review, covering phosphane-oxazoline ligands in catalysis, see: P. Braunstein, F. Naud, Angew. Chem. 2001, 113, 702; Angew. Chem. Int. Ed. 2001, 40, 681.
3. b) for a general review, covering phosphane-oxazoline ligands in catalysis, see: P. Braunstein, F. Naud, Angew. Chem. 2001, 113, 702; Angew. Chem. Int. Ed. 2001, 40, 681.
4. Reviews: a) W. A. Herrmann, Angew. Chem. 2002, 114, 1342; Angew. Chem. Int. Ed. 2002, 41, 1290;
5. Reviews: a) W. A. Herrmann, Angew. Chem. 2002, 114, 1342; Angew. Chem. Int. Ed. 2002, 41, 1290;
6. b) D. Bourissou, O. Guerret, F. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39;
7. c) W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2257; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162.
8. c) W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2257; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162.
9. Selected examples for palladium-catalyzed coupling reactions: a) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818; Angew. Chem. Int. Ed. 2003, 42, 3690;
10. Selected examples for palladium-catalyzed coupling reactions: a) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818; Angew. Chem. Int. Ed. 2003, 42, 3690;
11. b) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421; Angew. Chem. Int. Ed. 2002, 41, 1363;
12. b) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421; Angew. Chem. Int. Ed. 2002, 41, 1363;
13. c) G. A. Grasa, M. S. Viciu, J. Huang, C. Zhang, M. L. Trudell, S. P. Nolan, Organometallics 2002, 21, 2866;
14. d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741.
15. Selected examples of ruthenium-catalyzed olefin ring-closing metathesis: a) T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573; Angew. Chem. Int. Ed. 1999, 38, 2416;
16. Selected examples of ruthenium-catalyzed olefin ring-closing metathesis: a) T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573; Angew. Chem. Int. Ed. 1999, 38, 2416;
17. b) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247;
18. c) J. Huang, H. Z. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 5375;
19. d) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Hermann, Tetrahedron Lett. 1999, 40, 4787.
20. Review on N-heterocyclic carbene ligands in asymmetric catalysis: M. C. Perry, K. Burgess, Tetrahedron: Asymmetry 2003, 14, 951.
21. J. J. Van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954.
22. M. C. Perry, X. Cui, M. T. Powell, D. R. Hou, J. H. Reibenspies, K. Burgess, J. Am. Chem. Soc. 2003, 125, 113.
23. Herrmann et al. obtained enantiomeric excesses of up to 32% ee: W. A. Herrmann, L. J. Goossen, C. Kocher, G. R. J. Artus, Angew. Chem. 1996, 108, 2580; Angew. Chem. Int. Ed. Engl. 1996, 35, 2805.
24. Herrmann et al. obtained enantiomeric excesses of up to 32% ee: W. A. Herrmann, L. J. Goossen, C. Kocher, G. R. J. Artus, Angew. Chem. 1996, 108, 2580; Angew. Chem. Int. Ed. Engl. 1996, 35, 2805.
25. Enders et al. reported maximum enantiomeric excesses of 44% ee in hydrosilylation catalysis with chiral N-heterocyclic carbenes: a) D. Enders, H. Gielen, J. Runsink, K. Breuer, S. Brode, K. Boehn, Eur. J. Inorg. Chem. 1998, 913;
26. b) D. Enders, H. Gielen, J. Organomet. Chem. 2001, 617-618, 70.
27. a) For a review on asymmetric hydrosilylation, see: H. Nishiyama, K. Itoh, Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000, chap. 2.
28. b) V. César, S. Bellemin-Laponnaz, L. H. Gade, Organometallics 2002, 21, 5204.
29. For the synthesis of the 2-bromo-oxazoline, see: A. I. Meyers, K. A. Novachek, Tetrahedron Lett. 1996, 37, 1747.
30. We also recently reported a very efficient way to synthesize trisoxazolines using 2-bromooxazoline, see: a) S. Bellemin-Laponnaz, L. H. Gade, Chem. Commun. 2002, 1286;
31. b) S. Bellemin-Laponnaz, L. H. Gade, Angew. Chem. 2002, 114, 3623; Angew. Chem. Int. Ed. 2002, 41, 3473.
32. b) S. Bellemin-Laponnaz, L. H. Gade, Angew. Chem. 2002, 114, 3623; Angew. Chem. Int. Ed. 2002, 41, 3473.
33. C. Köcher, W. A. Herrmann, J. Organomet. Chem. 1997, 532, 261.
34. Due to the arrangement of the ligands, a stereogenic center at the metal atom is created leading to the existence of a possible second diastereoisomer. However, we were not able to detect any trace of the second diastereomer by classical spectroscopic methods.
35. Similar examples for the trans influence of carbene ligands, see: a) A. R. Chianese, X. Li, M. C. Janzen, J. W. Faller, R. H. Crabtree, Organometallics 2003, 22, 1663;
36. b) J. A. Loch, M. Albrecht, E. Peris, J. Mata, J. W. Faller, R. H. Crabtree, Organometallics 2002, 21, 700;
37. c) A. C. Hillier, H. M. Lee, E. D. Stevens, S. P. Nolan, Organometallics 2001, 20, 4246.
38. Fu and Tao reported a new P,N ligand family giving high enantioselectivities: B. Tao, G. C. Fu, Angew. Chem. 2002, 114, 4048; Angew. Chem. Int. Ed. 2002, 41, 3892.
39. Fu and Tao reported a new P,N ligand family giving high enantioselectivities: B. Tao, G. C. Fu, Angew. Chem. 2002, 114, 4048; Angew. Chem. Int. Ed. 2002, 41, 3892.
40. Evans et al. reported a new P,S ligand family giving very high activity and selectivity in Rh-catalyzed hydrosilylation: D. A. Evans, F. E. Michael, J. S. Tedrow, K. R. Campos, J. Am. Chem. Soc. 2003, 125, 3534.
41. The influence of the silane structure on the enantioselectivity of the reaction was investigated and we found that the standard reducing agent diphenylsilane gave the best results.
42. a) R. Kuwano, M. Sawamura, J. Shirai, M. Takahashi, Y. Ito, Bull. Chem. Soc. Jpn. 2000, 73, 485, and references therein;
43. Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988.
44. Note added in proof (14.1.2004); While this work was in press an efficient chiral biscarbene-rhodium hydrosilylation catalyst was reported: W.-L. Duan, M. Shi, G. B. Rong, Chem. Commun. 2003, 2916.