Chiral, chelating, hydroxyalkyl and hydroxyaryl n-heterocyclic carbenes: Design, synthesis, and application in copper-catalyzed asymmetric conjugate addition (Cu-ACA)

Aldrichimica Acta

Volumn 42, Issue 2, 2009, Pages 43-50

  Wencel, Joanna ^a   Mauduit, Marc ^a   Hénon, Hélène ^b   Kehrli, Stefan ^b   Alexakis, Alexandre ^b  

^a UNIVERSITÉ EUROPÉENNE DE BRETAGNE   (France)

^b UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Asymmetric conjugate addition; Chiral quaternary centers; Copper catalysis; N heterocyclic carbenes; Organometallic reagents

Indexed keywords

EID: 70449717682     PISSN: 00025100     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

1. Öfele, K. J. Organomet. Chem. 1968, 12, P42.
2. Wanzlick, H.-W.; Schönherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141.
3. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
4. For recent books dealing with NHCs in synthesis and catalysis, see: (a) N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; WileyVCH: Weinheim, 2006.
5. (b) N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry Series; Springer: Berlin, 2007; Vol.21.
6. For recent reviews on chiral NHCs, see: (a) Mauduit, M.; Clavier, H. In N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; WileyVCH: Weinheim, 2006; pp 183-222.
7. (b) Gade, L. H.; BelleminLaponnaz, S. In N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry Series; Springer: Berlin, 2007; Vol.21, pp 117-157.
8. NHC ligands 3 and 4 have been extensively studied in both coppercatalyzed Asymmetric Allylic Alkylation (AAA) and rutheniumcatalyzed Asymmetric Olefin Metathesis (AOM):
9. (a) Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954 (synthesis of 3).
10. (b) Kacprzynski, M. A.; May T. L.; Kazane, S. A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 4554 and references therein.
11. SIMes-leucinol (2a) and its SIPr analogue have recently been used in the copper-catalyzed Asymmetric Allylic Alkylation (AAA) with up to 96% ee's: Jennequin, T.; Daubignard, J.; Wencel, J.; Crévisy, C.; Mauduit, M. École Nationale Supérieure de Chimie de Rennes, Rennes, France. Unpublished work, 2008.
12. Arnold, P. L.; Rodden, M.; Davis, K. M.; Scarisbrick, A. C.; Blake, A. J.; Wilson, C. Chem. Commun. 2004, 1612.
13. For recent reviews on enantioselective Cu-catalyzed conjugate additions, see: (a) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221.
14. (b) Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796.
15. For an example, see Seo, H.; Park, H.-j.; Kim, B. Y.; Lee, J. H.; Son, S. U.; Chung, Y. K. Organometallics 2003, 22, 618.
16. (a) Clavier, H.; Coutable, L.; Guillemin, J.-C.; Mauduit, M. Tetrahedron: Asymmetry 2005, 16, 921.
17. (b) Clavier, H.; Coutable, L.; Toupet, L.; Guillemin, J.-C.; Mauduit, M. J. Organomet. Chem. 2005, 690, 5237.
18. (c) Rix, D.; Labat, S.; Toupet, L.; Crévisy, C.; Mauduit, M. Eur. J. Inorg. Chem. 2009, 1989.
19. Larsen, A. O.; Leu, W.; Oberhuber, C. N.; Campbell, J. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 11130.
20. Van Veldhuizen, J. J.; Campbell, J. E.; Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 6877.
21. See for example: (a) Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178.
22. (b) Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400.
23. (c) Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427.
24. Fraser, P. K.; Woodward, S. Tetrahedron Lett. 2001, 42, 2747.
25. Alexakis, A.; Winn, C. L.; Guillen, F.; Pytkowicz, J.; Roland, S.; Mangeney, P. Adv. Synth. Catal. 2003, 345, 345.
26. For examples, see: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779.
27. (b) Ducan, A. P.; Leighton, J. L. Org. Lett. 2004, 6, 4117.
28. (c) Wencel, J.; Rix, D.; Jennequin, T.; Labat, S.; Crévisy, C.; Mauduit, M. Tetrahedron: Asymmetry 2008, 19, 1804.
29. Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473.
30. Posner, G. H. Org. React. 1972, 19, 1.
31. Lee, K.-s.; Brown, M. K.; Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc. 2006, 128, 7182.
32. (a) D'Augustin, M.; Palais, L.; Alexakis, A. Angew. Chem., Int. Ed. 2005, 44, 1376.
33. (b) Vuagnoux-d'Augustin, M.; Alexakis, A. Chem.-Eur. J. 2007, 13, 9647.
34. (c) Hawner, C.; Li, K.; Cirriez, V.; Alexakis, A. Angew. Chem., Int. Ed. 2008, 47, 8211.
35. A remarkable design of chelating sulfonate-NHCs and their application in Cu-ACA were recently reported: (a) Brown, M. K.; May, T. L.; Baxter, C. A.; Hoveyda A. H. Angew. Chem., Int. Ed. 2007, 46, 1097.
36. (b) May, T. L.; Brown, M. K.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2008, 47, 7358.
37. For a recent review, see Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824.
38. Kehrli, S.; Alexakis, A. University of Geneva, Geneva, Switzerland. Unpublished work, 2008.
39. Martin, D.; Kehrli, S.; d'Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A.J. Am. Chem. Soc. 2006, 128, 8416.
40. For a review on asymmetric conjugate addition that creates quaternary all-carbon centers, see Alexakis, A.; Vuagnoux-d'Augustin, M.; Martin, D.; Kehrli, S.; Palais, L.; Hénon, H.; Hawner, C. Chimia 2008, 62, 461.
41. Hayashi, T.; Yamamoto, S.; Tokunaga, N. Angew. Chem., Int. Ed. 2005, 44, 4224.
42. Hénon, H.; Mauduit, M.; Alexakis, A. Angew. Chem., Int. Ed. 2008, 47, 9122.
43. Krause, N.; Thorand, S. Inorg. Chim. Acta 1999, 296, 1.
44. Racemic total syntheses of natural products (vibsane family) bearing chiral quartenary centers (using a Cu-catalyzed conjugate addition step involving Grignard reagents and 3-methyl-2cyclohexenone) have recently been reported: (a) Heim, R.; Wiedemann, S.; Williams, C. M.; Bernhardt, P. V. Org. Lett. 2005, 7, 1327.
45. (b) Gallen, M. J.; Williams, C. M. Org. Lett. 2008, 10, 713.
46. (c) Chen, A. P.-J.; Williams, C. M. Org. Lett. 2008, 10, 3441.