Asymmetric conjugate addition to α-substituted enones/enolate trapping

Organic Letters

Volumn 16, Issue 1, 2014, Pages 118-121

  Germain, Nicolas ^a   Guénée, Laure ^a   Mauduit, Marc ^b   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84891805416     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403104s     Document Type: Article

References (40)

1. Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796
2. Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824
3. Vuagnoux-d'Augustin, M.; Alexakis, A. Chem.-Eur. J. 2007, 13, 9647 and references therein
4. For a review on Mauduit-type NHCs, see: Wencel, J.; Mauduit, M.; Hénon, H.; Kehrli, S.; Alexakis, A. Aldrichimica Acta 2009, 42, 43
5. Ngoc, D. T.; Albicker, M.; Schmeider, L.; Cramer, N. Org. Biomol. Chem. 2010, 8, 1781
6. Gärtner, M.; Qu, J.; Helmchen, G. J. Org. Chem. 2012, 77, 1186
7. Silva, A. L.; Toscano, R. A.; Maldonado, L. A. J. Org. Chem. 2013, 78, 5282
8. Chapdelaine, M. J.; Hulce, M. Org. React. 1990, 38, 227
9. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841
10. Tomioka, K.; Kawasaki, H.; Yasuda, K.; Koga, K. J. Am. Chem. Soc. 1988, 110, 3597
11. Corey, E. J.; Guzman-Perez, A. Angew. Chem. 1998, 110, 402
12. Angew. Chem., Int. Ed. 1998, 37, 388.
13. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363
14. Baro, A.; Christoffers, J. Adv. Synth. Catal. 2005, 347, 1473
15. Trost, B. M.; Jiang, C. Synlett 2006, 3, 369
16. Hawner, C.; Alexakis, A. Chem. Commun. 2010, 46, 7295
17. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593
18. Soorukram, D.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3686
19. Trost, B. M.; Yasukat, T. J. Am. Chem. Soc. 2001, 123, 7162
20. Kano, T.; Hayashi, Y.; Maruoka, K. J. Am. Chem. Soc. 2013, 135, 7134
21. Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195
22. Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918
23. Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829
24. Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 62
25. Hong, A. Y.; Stoltz, B. M. Eur. J. Org. Chem. 2013, 14, 2745
26. Trost, B. M.; Xu, J.; Schmidt, T. J. Am. Chem. Soc. 2009, 131, 18343
27. Nakamura, M.; Hajra, A.; Endo, K.; Nakamura, E. Angew. Chem., Int. Ed. 2005, 44, 7248
28. Weatzig, S. R.; Rayabarapu, D. K.; Weaver, J. D.; Tunge, J. D. Angew. Chem., Int. Ed. 2006, 45, 4977
29. Nahra, F.; Mace, Y.; Lambin, D.; Riant, O. Angew. Chem., Int. Ed. 2013, 52, 3208
30. 2 exemplifies the importance of studying the influence of longer α-alkyl chain: Scher, J. U.; Pillinger, M. H. Clin. Immunol. 2005, 114, 100
31. Peng, F.; Grote, R. E.; Wilson, R. M.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 10904
32. CCDC 961181 contains all of the crystallographic data for this paper. This data is available free of charge from the Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data-request/cif. See the Supporting Information.
33. Walsh, P. J.; Kozlowski, M. C. Fundamentals of Asymmetric Catalysis; University Science Books: Sausalito, 2009; pp 674. For an example of a double-diastereoselective process starting from an enriched mixture of enantiomers, see
34. Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A. Eur. J. Org. Chem. 2003, 1428
35. During the course of our studies, the construction of contiguous exocyclic tertiary-quaternary centers appeared; see: Liu, W.-B.; Reeves, C. M.; Virgil, S. C.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 10626
36. Williams, D. R.; Heidebrecht, R. W., Jr. J. Am. Chem. Soc. 2003, 125, 1843
37. Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11
38. For the synthesis of (+)-confertin, Quinkert et al. developed a procedure using 6 equiv of (S)-2-ethoxymethylpyrrolidine for the addition of isopropenyllithium to 2-methylcyclopentenone. See: Quinkert, G.; Müller, T.; Königer, A.; Schultheis, O.; Sickenberger, B.; Dürner, G. Tetrahedron Lett. 1992, 33, 3469
39. Mandal, M.; Yun, H.; Dudley, G. B.; Lin, S.; Tran, D. S.; Danishefsky, S. J. J. Org. Chem. 2005, 70, 10619
40. Hamilton, R. J.; Mander, L. N.; Sethi, S. P. Tetrahedron 1986, 42, 2881