A new organocatalytic concept for asymmetric -alkylation of aldehydes

Journal of the American Chemical Society

Volumn 136, Issue 45, 2014, Pages 15929-15932

  Caruana, Lorenzo ^a   Kniep, Florian ^a   Johansen, Tore Kiilerich ^a   Poulsen, Pernille H ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ORGANIC POLYMERS;

CONTIGUOUS STEREOCENTERS; DIASTEREOCONTROL; ENAMINES; ORGANOCATALYTIC; P-QUINONE METHIDES; SECONDARY AMINES;

ALDEHYDES;

ALDEHYDE DERIVATIVE; ENAMINE; QUINONE DERIVATIVE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPIMERIZATION; REACTION TIME; SCREENING; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 84910010881     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja510475n     Document Type: Article

References (55)

1. Vesely, J.; Rios, R. ChemCatChem 2012, 4, 942
2. Hodgson, D. M.; Charlton, A. Tetrahedron 2014, 70, 2207
3. MacMillan, D. W. C. Nature 2008, 455, 304
4. Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 1360
5. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167
6. Cheong, P. H. Y.; Legault, C. Y.; Um, J. M.; Celebi-Olcum, N.; Houk, K. N. Chem. Rev. 2011, 111, 5042
7. Jensen, K. L. Dickmeiss, G. Jiang, H. Albrecht, A.Jrgensen, K. A. Acc. Chem. Res. 2012, 45, 248
8. Mukherjee, S.; Yang, J.-W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471
9. Nielsen, M.; Worgull, D.; Zweifel, T.; Gschwend, B.; Bertelsen, S.; Jørgensen, K. A. Chem. Commun. 2011, 47, 632
10. Beeson, T. D.; Mastracchio, A.; Hong, J. B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582
11. MacMillan, D. W. C.; Rendler, S. Enantioselective Organo-SOMO Catalysis: A Novel Activation Mode for Asymmetric Synthesis. In Asymmetric Synthesis II: More Methods and Applications; Christmann, M.; Brase, S., Eds.; Wiley: New York, 2012; p 87.
12. Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450 (intramolecular)
13. List, B. Coric, I. Grygorenko, O. O. Kaib, P. S. J. Komarov, I. Lee, A. Leutzsch, M. Pan, S. C. Tymtsunik, A. V. Gemmerem, M. Angew. Chem., Int. Ed. 2014, 53, 282
14. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77
15. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322
16. Arceo, E.; Jurberg, I. D.; álvarez-Fernández, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750
17. Arceo, E.; Bahamonde, A.; Bergonzini, G.; Melchiorre, P. Chem. Sci. 2014, 5, 2438
18. Riente, P.; Adams, A. M.; Albero, J.; Palomares, E.; Pericas, M. A. Angew. Chem., Int. Ed. 2014, 53, 9613
19. Cozzi, P. G.; Benfatti, F.; Zoli, L. Angew. Chem., Int. Ed. 2009, 48, 1313
20. Benfatti, F.; Capdevila, M. G.; Zoli, L.; Benedetto, E.; Cozzi, P. G. Chem. Commun. 2009, 5919
21. Benfatti, F.; Benedetto, E.; Cozzi, P. G. Chem.-Asian J. 2010, 5, 2047
22. Zhang, L.; Cui, L.; Li, X.; Li, J.; Luo, S.; Cheng, J.-P. Chem.-Eur. J. 2010, 16, 2045
23. Stiller, J.; Marques Lopez, E.; Herrera, R. P.; Frohlich, R.; Strohmann, C.; Christmann, M. Org. Lett. 2011, 13, 70
24. Xiao, J. Org. Lett. 2012, 14, 1716
25. Guiteras Capdevila, M.; Emer, E.; Benfatti, F.; Gualandi, A.; Wilson, C. M.; Cozzi, P. G. Asian J. Org. Chem. 2012, 1, 38
26. Xiao, J.; Zhao, K.; Loh, T.-P. Chem. Commun. 2012, 48, 3548
27. Brown, R. A.; Kuo, W. H.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 9286
28. Wagner, H.-U.; Gompper, R. Quinone Methides in The Chemistry of the Quinonoid Compounds, Vol. 2; Patai, S., Ed.; Wiley: New York, 1974; Chap. 18, p 1145.
29. Quinone Methides; Rokita, S. E., Ed.; Wiley: Hoboken, NJ, 2009.
30. Toteva, M. M.; Richard, J. P. Adv. Phys. Org. Chem. 2011, 45, 39
31. Takao, K.-I.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.-I.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291
32. Barragán-Huerta, B. E.; Peralta-Cruz, J.; González-Laredo, R. F.; Karchesy, J. Phytochemistry 2004, 65, 925
33. Martin, H. J.; Magauer, T.; Mulzer, J. Angew. Chem., Int. Ed. 2010, 122, 5746
34. Jansen, R.; Gerth, K.; Steinmetz, H.; Reinecke, S.; Kessler, W.; Kirschning, A.; Muller, R. Chem.-Eur. J. 2011, 17, 7739
35. Larsen, A. A. Nature 1969, 224, 25
36. Hamels, D.; Dansette, P. M.; Hillard, E. A.; Top, S.; Vessieres, A.; Herson, P.; Jaouen, G.; Mansuy, D. Angew. Chem., Int. Ed. 2009, 48, 9124
37. Messiano, G. B.; da Silva, T.; Nascimento, I. R.; Lopes, L. M. X. Phytochemistry 2009, 70, 590
38. Dehn, R.; Katsuyama, Y.; Weber, A.; Gerth, K.; Jansen, R.; Steinmetz, H.; Hofle, G.; Muller, R.; Kirschning, A. Angew. Chem., Int. Ed. 2011, 50, 3882
39. Sridar, C.; DAgostino, J.; Hollenberg, P. F. Drug. Metab. Dispos. 2012, 40, 2280
40. Richter, D.; Hampel, N.; Singer, T.; Ofial, A. R.; Mayr, H. Eur. J. Org. Chem. 2009, 3203
41. Amouri, H.; Le, Bras J. Acc. Chem. Res. 2002, 35, 501
42. Pathak, T. P.; Sigman, M. S. J. Org. Chem. 2011, 76, 9210
43. Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18, 9160
44. Asymmetric catalytic 1,6-conjugated addition of malonates to p -quinone methides: Chu, W.-D.; Zhang, L.-F.; Bao, X.; Zhao, X.-Y.; Zeng, C.; Du, J.-Y.; Zhang, G.-B.; Wang, F.-X.; Ma, X.-Y.; Fan, C.-A. Angew. Chem., Int. Ed. 2013, 52, 9229
45. Nakagaki, N.; Uno, T.; Kubo, M.; Itoh, T. J. Polym. Sci. Part A 2009, 47, 5923
46. Lizuka, S.; Nakagaki, N.; Uno, T.; Kubo, M.; Itoh, T. Macromolecules 2010, 43, 6962
47. Nagai, T.; Uno, T.; Kubo, M.; Itoh, T. J. Polym. Sci. Part A 2012, 50, 466
48. Csáky, A. G.; de La Herrán, G.; Murcia, M. C. Chem. Soc. Rev. 2010, 39, 4080
49. Biju, A.T. ChemCatChem 2011, 3, 1847
50. Silva, E. M. P.; Silva, A. M. S. Synthesis 2012, 3109
51. Tian, X.; Liu, Y.; Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 6439
52. Dellamico, L. Albrecht, A . Naicker, T. Poulsen, P. H. Jrgensen, K. A. J. Am. Chem. Soc. 2013, 135, 8063
53. Chiang, Y.; Kresge, A. J.; Zhu, Y. J. Am. Chem. Soc. 2002, 124, 6349
54. The t Bu group is often used as a bulky protecting group in the synthesis of aromatic compounds. For a review on the role of t Bu and de- tert -butylation strategies, see: Saleh, S. A.; Tashtoush, H. I. Tetrahedron 1998, 54, 14157
55. For a review on Henry and aza-Henry reactions, see: Nagasawa, K.; Sohtome, Y. In Comprehensive Chirality, Vol. 6; Carreira, E. M.; Yamamoto, H., Eds.; Elsevier: Amsterdam, 2012; p 157.