Asymmetric Synthesis with N-Heterocyclic Carbenes. Application to the Copper-Catalyzed Conjugate Addition

Advanced Synthesis and Catalysis

Volumn 345, Issue 3, 2003, Pages 345-348

  Alexakis, Alexandre ^a   Winn, Caroline L ^a   Guillen, Frederic ^a   Pytkowicz, Julien ^b   Roland, Sylvain ^b   Mangeney, Pierre ^b  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

Asymmetry; Conjugate addition; Copper; Dialkylzinc; Michael acceptors; N heterocyclic carbenes

Indexed keywords

COPPER; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; LIGAND; REAGENT; ZINC DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHIRALITY; CONJUGATE; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY;

EID: 0038560230     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200390037     Document Type: Article

References (40)

1. a) D. J. Cardin, B. Cetinkaya, M. F. Lappert, Chem. Rev. 1972, 72, 545;
2. b) W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 1997, 36, 2162;
3. c) T. Weskamp, V. P. W. Böhm, W. A. Herrmann, J. Organomet. Chem. 2000, 600, 12;
4. d) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39;
5. e) L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181.
6. W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2002, 41, 1291 and references cited therein.
7. For some Cu complexes see: a) P. L. Arnold, A. C. Scarisbrick, A. J. Blake, C. Wilson, Chem. Commun. 2001, 2340; b) A. A. D. Tulloch, A.A. Danopoulos, S. Kleinhez, M. E. Light, M. B. Hursthouse, G. Eastham, Organometallics 2001, 20, 2027 and references cited therein. For Ag complexes see: H. M. J. Wang, I. J. B. Lin, Organometallics 1998, 17, 972 and references cited therein.
8. For some Cu complexes see: a) P. L. Arnold, A. C. Scarisbrick, A. J. Blake, C. Wilson, Chem. Commun. 2001, 2340; b) A. A. D. Tulloch, A.A. Danopoulos, S. Kleinhez, M. E. Light, M. B. Hursthouse, G. Eastham, Organometallics 2001, 20, 2027 and references cited therein. For Ag complexes see: H. M. J. Wang, I. J. B. Lin, Organometallics 1998, 17, 972 and references cited therein.
9. For some Cu complexes see: a) P. L. Arnold, A. C. Scarisbrick, A. J. Blake, C. Wilson, Chem. Commun. 2001, 2340; b) A. A. D. Tulloch, A.A. Danopoulos, S. Kleinhez, M. E. Light, M. B. Hursthouse, G. Eastham, Organometallics 2001, 20, 2027 and references cited therein. For Ag complexes see: H. M. J. Wang, I. J. B. Lin, Organometallics 1998, 17, 972 and references cited therein.
10. For selected references see: a) C. A. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69; b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 1602; c) B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 5689; d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741; e) T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 1999, 38, 2416; f) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; g) H. M. Lee, D. C. Smith Jr., Z. He, E. D. Stevens, C. S. Yi, S. P. Nolan, Organometallics 2001, 20, 794; h) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201.
11. For selected references see: a) C. A. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69; b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 1602; c) B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 5689; d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741; e) T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 1999, 38, 2416; f) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; g) H. M. Lee, D. C. Smith Jr., Z. He, E. D. Stevens, C. S. Yi, S. P. Nolan, Organometallics 2001, 20, 794; h) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201.
12. For selected references see: a) C. A. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69; b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 1602; c) B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 5689; d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741; e) T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 1999, 38, 2416; f) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; g) H. M. Lee, D. C. Smith Jr., Z. He, E. D. Stevens, C. S. Yi, S. P. Nolan, Organometallics 2001, 20, 794; h) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201.
13. For selected references see: a) C. A. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69; b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 1602; c) B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 5689; d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741; e) T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 1999, 38, 2416; f) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; g) H. M. Lee, D. C. Smith Jr., Z. He, E. D. Stevens, C. S. Yi, S. P. Nolan, Organometallics 2001, 20, 794; h) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201.
14. For selected references see: a) C. A. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69 ; b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 1602; c) B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 5689; d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741; e) T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 1999, 38, 2416; f) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; g) H. M. Lee, D. C. Smith Jr., Z. He, E. D. Stevens, C. S. Yi, S. P. Nolan, Organometallics 2001, 20, 794; h) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201.
15. For selected references see: a) C. A. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69; b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 1602; c) B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 5689; d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741; e) T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 1999, 38, 2416; f) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; g) H. M. Lee, D. C. Smith Jr., Z. He, E. D. Stevens, C. S. Yi, S. P. Nolan, Organometallics 2001, 20, 794; h) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201.
16. For selected references see: a) C. A. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69; b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 1602; c) B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 5689; d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741; e) T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 1999, 38, 2416; f) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; g) H. M. Lee, D. C. Smith Jr., Z. He, E. D. Stevens, C. S. Yi, S. P. Nolan, Organometallics 2001, 20, 794; h) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201.
17. For selected references see: a) C. A. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69; b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 1602; c) B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 5689; d) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741; e) T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 1999, 38, 2416; f) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; g) H. M. Lee, D. C. Smith Jr., Z. He, E. D. Stevens, C. S. Yi, S. P. Nolan, Organometallics 2001, 20, 794; h) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201.
18. a) W. A. Herrmann, L. J. Goossen, C. Köcher, G. R. J. Artus,. Angew. Chem. Int. Ed. Engl. 1996, 35, 2805;
19. b) D. Enders, H. Gielen, J. Organomet. Chem. 2001, 617-618, 70 and references cited therein;
20. c) S. Lee, J. F. Hartwig, J. Org. Chem. 2001, 66, 3402;
21. d) T. J. Seiders, D. W. Ward, R. H. Grubbs, Org. Lett. 2001, 3, 3225;
22. e) M. T. Powell, D.-R. Hou, M. C. Perry, X. Cui, K. Burgess, J. Am. Chem. Soc. 2001, 123, 8878;
23. f) D. S. Clyne, J. Jin, E. Genest, J. C. Galluci, T. V. RajanBabu, Org. Lett. 2000, 2, 1125;
24. g) J. J. Van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954.
25. P. K. Fraser, S. Woodward, Tetrahedron Lett. 2001, 42, 2747.
26. a) A. J. Arduengo III, R. L. Harlow, M. A. Kline, J. Am. Chem. Soc. 1991, 113, 361;
27. b) A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913.
28. F. Guillen, C. L. Winn, A. Alexakis, Tetrahedron Asymmetry 2001, 12, 2083.
29. J. Pytkowicz, S. Roland, P. Mangeney, Tetrahedron Asymmetry 2001, 12, 2087.
30. a) A. Alexakis, J. Frutos, P. Mangeney, Tetrahedron Asymmetry 1993, 4, 2427;
31. b) A. H. M. De Vries, A. Meetsma, B. L. Feringa, Angew. Chem. Int. Ed. Engl. 1996, 35, 2374;
32. c) A. Alexakis, J. Vastra, P. Mangeney, Tetrahedron Lett. 1997, 38, 7745;
33. d) B. L. Feringa, Acc. Chem. Res. 2000, 33, 346.
34. A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc., 2002, 124, 5262.
35. Imidazolium salts 6-8 were prepared in a similar way to 5, according to: W. A. Herrmann, M. Elison, J. Fischer, C. Kocher, G. R. J. Artus, Chem. Eur. J. 1996, 2, 777.
36. Silver carbenes 9-13 were prepared in a similar way to 2, according to: J. Pytkowicz, S. Roland, P. Mangeney, J. Organomet. Chem. 2001, 631, 157.
37. [13]
38. For a review on the copper-catalyzed asymmetric conjugate addition, with a list of all tested substrates, see: A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221; for other reviews on the same topic: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171.
39. For a review on the copper-catalyzed asymmetric conjugate addition, with a list of all tested substrates, see: A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221; for other reviews on the same topic: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171.
40. For a review on the copper-catalyzed asymmetric conjugate addition, with a list of all tested substrates, see: A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221; for other reviews on the same topic: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171.