Highly chemo- and enantioselective cross-benzoin reaction of aliphatic aldehydes and α-ketoesters

Organic Letters

Volumn 15, Issue 9, 2013, Pages 2214-2217

  Thai, Karen ^a   Langdon, Steven M ^a   Bilodeau, François ^b   Gravel, Michel ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84877148947     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400769t     Document Type: Article

References (46)

1. Enders, D.; Balensiefer, T.; Niemeier, O.; Christmann, M. In Enantioselective Organocatalysis: Reactions and Experimental Procedures; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, Germany, 2007; pp 331-355.
2. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606
3. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2009, 291, 77
4. Chiang, P.-C.; Bode, J. W. In N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools; Díez-González, S., Ed.; Royal Society of Chemistry: Cambridge, United Kingdom, 2010; pp 339-445.
5. Campbell, C. D.; Ling, K. B.; Smith, A. D. In N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis; Cazin, C. S. J., Ed.; Springer: Dortrecht, Germany, 2011; Vol. 32, pp 263-297.
6. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
7. Ukai, T.; Tanaka, S.; Dokawa, S. J. Pharm. Soc. Jpn. 1943, 63, 269
8. Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743
9. Ma, Y.; Wei, S.; Wu, J.; Yang, F.; Liu, B.; Lan, J.; Yang, S.; You, J. Adv. Synth. Catal. 2008, 350, 2645
10. Enders, D.; Han, J. Tetrahedron: Asymmetry 2008, 19, 1367
11. Baragwanath, L.; Rose, C. A.; Zeitler, K.; Connon, S. J. J. Org. Chem. 2009, 74, 9214
12. Soeta, T.; Tabatake, Y.; Inomata, K.; Ukaji, Y. Tetrahedron 2012, 68, 894
13. Stetter, H.; Dämbkes, G. Synthesis 1977, 403
14. Mennen, S. M.; Miller, S. J. J. Org. Chem. 2007, 72, 5260
15. Rose, C. A.; Gundala, S.; Connon, S. J.; Zeitler, K. Synthesis 2011, 190
16. Mathies, A. K.; Mattson, A. E.; Scheidt, K. A. Synlett 2009, 377
17. Bortolini, O.; Fantin, G.; Fogagnolo, M.; Giovannini, P. P.; Venturi, V.; Pacifico, S.; Massi, A. Tetrahedron 2011, 67, 8110
18. Tarr, J. C.; Johnson, J. S. J. Org. Chem. 2010, 75, 3317 and references therein
19. Enders, D.; Grossmann, A.; Fronert, J.; Raabe, G. Chem. Commun. 2010, 46, 6282
20. O'Toole, S. E.; Rose, C. A.; Gundala, S.; Zeitler, K.; Connon, S. J. J. Org. Chem. 2011, 76, 347
21. Jin, M. Y.; Kim, S. M.; Han, H.; Ryu, D. H.; Yang, J. W. Org. Lett. 2011, 13, 880
22. Rose, C. A.; Gundala, S.; Fagan, C. -L.; Franz, J. F.; Connon, S. J.; Zeitler, K. Chem. Sci. 2012, 3, 735
23. Giovannini, P. P.; Fantin, G.; Massi, A.; Venturi, V.; Pedrini, P. Org. Biomol. Chem. 2011, 9, 8038
24. Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432
25. Enders, D.; Niemeier, O. Synlett 2004, 2111
26. Enders, D.; Niemeier, O.; Raabe, G. Synlett 2006, 2431
27. Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem., Int. Ed. 2006, 45, 1463
28. Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Angew. Chem., Int. Ed. 2006, 45, 3492
29. Takikawa, H.; Suzuki, K. Org. Lett. 2007, 9, 2713
30. Li, Y.; Feng, Z.; You, S.-L. Chem. Commun. 2008, 2263
31. Ema, T.; Oue, Y.; Akihara, K.; Miyazaki, Y.; Sakai, T. Org. Lett. 2009, 11, 4866
32. Takada, A.; Hashimoto, Y.; Takikawa, H.; Hikita, K.; Suzuki, K. Angew. Chem., Int. Ed. 2011, 50, 2297
33. Pohl, M.; Lingen, B.; Müller, M. Chem.-Eur. J. 2002, 8, 5288
34. Dünkelmann, P.; Kolter-Jung, D.; Nitsche, A.; Demir, A. S.; Siegert, P.; Lingen, B.; Baumann, M.; Pohl, M.; Müller, M. J. Am. Chem. Soc. 2002, 124, 12084
35. Lehwald, P.; Richter, M.; Röhr, C.; Hung-wen, L.; Müller, M. Angew. Chem., Int. Ed. 2010, 49, 2389
36. Beigi, M.; Waltzer, S.; Fries, A.; Eggeling, L.; Sprenger, G. A.; Müller, M. Org. Lett. 2013, 15, 452
37. Müller, C.; Pérez-Sánchez, M.; Domínguez de María, P. Org. Biomol. Chem. 2013, 11, 2000
38. DiRocco, D. A.; Noey, E. L.; Houk, K. N.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 2391
39. DiRocco, D. A.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 5904
40. Sánchez-Larios, E.; Thai, K.; Bilodeau, F.; Gravel, M. Org. Lett. 2011, 13, 4942
41. Cohen, D. T.; Cardinal-David, B.; Scheidt, K. A. Angew. Chem., Int. Ed. 2011, 50, 1678
42. DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. J. Am. Chem. Soc. 2009, 31, 10872
43. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5726
44. An analogous N -Ph salt has been reported: Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298
45. Dudding, T.; Houk, K. N. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5770
46. Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem., Int. Ed. 2006, 45, 1463