Enantio- and diastereoselective organocatalytic α-alkylation of aldehydes with 3-substituted 2-(bromomethyl)acrylates

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 747-753

  Jiménez, Jacqueline ^a,b   Landa, Aitor ^a   Lizarraga, Aitziber ^a   Maestro, Miguel ^a,c   Mielgo, Antonia ^a   Oiarbide, Mikel ^a   Velilla, Irene ^a   Palomo, Claudio ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^c UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENES; DIASTEREOSELECTIVE; ENANTIO; ENANTIOPURITY; ESTER GROUPS; FUNCTIONALIZED; OPTIMUM CONDITIONS; ORGANOCATALYSTS; ORGANOCATALYTIC;

ALDEHYDES; ALKYLATION; ORGANIC COMPOUNDS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

SALTS;

2 (BROMOMETHYL)ACRYLATE; ALDEHYDE DERIVATIVE; CYCLOPENTENE DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84855535325     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202073n     Document Type: Article

References (48)

1. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000.
2. Hughes, D. L. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. III, pp 1273-1294, and Supplement 1, 2004, p. 161-169.
3. Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253-2329
4. Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 1360-1363
5. Alba, A. N.; Viciano, M.; Rios, R. Chem. Cat. Chem. 2009, 1, 437-439
6. Weix, D. J.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7720-7721
7. Pd/Brønsted acid asymmetric catalysis: Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336-13337
8. Pd/pyrrolidine catalysis: Ibrahem, I.; Córdova, A. Angew. Chem., Int. Ed. 2006, 45, 1952-1956
9. Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451
10. Fu, A.; List, B.; Thiel, W. J. Org. Chem. 2006, 71, 320-326
11. Lv, J.; Zhang, J.; Lin, Z.; Wang, Y. Chem.-Eur. J. 2009, 15, 972-979
12. Rios, R.; Sundén, H.; Vesely, J.; Zhao, G.-L.; Dziedzic, P.; Córdova, A. Adv. Synth. Catal. 2007, 349, 1028-1032
13. Xie, H.; Zu, L.; Li, H.; Wang, J.; Wang, W. J. Am. Chem. Soc. 2007, 129, 10886-10894
14. Terrasson, V.; Van der Lee, A.; De Figueiredo, R. M.; Campagne, J. M. Chem.-Eur. J. 2010, 16, 7875-7880
15. Ibrahem, I.; Zhao, G.-L.; Rios, R.; Vesely, J.; Sundén, H.; Dziedzic, P.; Córdova, A. Chem.-Eur. J. 2008, 14, 7867-7879
16. Enders, D.; Wang, C.; Bats, J. W. Angew. Chem., Int. Ed. 2008, 47, 7539-7542
17. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77-79
18. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875-10877
19. Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582-585
20. Um, J. M.; Gutierrez, O.; Schoenebeck, F.; Houk, K. N.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 6001-6005 and references cited therein
21. Nicolaou, K. C.; Reingruber, R.; Sarlah, D.; Bräse, S. J. Am. Chem. Soc. 2009, 131, 2086-2087
22. Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 4260-4263
23. Benfatti, F.; Capdevila, M. G.; Zoli, L.; Benedetto, E.; Cozzi, P. G. Chem. Commun. 2009, 5919-5921
24. Neumann, M.; Füldner, S.; König, B.; Zeitler, K. Angew. Chem., Int. Ed. 2011, 50, 951-954
25. Zhang, B.; Xiang, S.-K.; Zhang, L.-H.; Cui, Y.; Jiao, N. Org. Lett. 2011, 13, 5212-5215
26. Ikeda, M.; Miyake, Y.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2010, 49, 7289-7293
27. Sinisi, R.; Vita, M. V.; Gualandi, A.; Emer, E.; Cozzi, P. G. Chem.-Eur. J. 2011, 17, 7404-7408
28. Yoshida, A.; Ikeda, M.; Hattori, G.; Miyake, Y.; Nishibayashi, Y. Org. Lett. 2011, 13, 592-595
29. Cozzi, P. G.; Benffati, F.; Zoli, L. Angew. Chem., Int. Ed. 2009, 48, 1313-1316
30. Zhang, L.; Cui, L.; Li, X.; Li, J.; Luo, S.; Cheng, J.-P. Chem.-Eur. J. 2010, 16, 2045-2049
31. Xiang, S.-K.; Zhang, B.; Zhang, L. H.; Cui, Y.; Jiao, N. Chem. Commun. 2011, 47, 5007-5009
32. Stiller, J.; Marqués-López, E.; Herrera, R. P.; Fröhlich, R.; Strohman, C.; Christman, M. Org. Lett. 2011, 13, 70-73
33. Bergonzini, G.; Vera, S.; Melchiorre, P. Angew. Chem., Int. Ed. 2010, 49, 9685-9688
34. Gualandi, A.; Emer, E.; Capdevila, M. G.; Cozzi, P. G. Angew. Chem., Int. Ed. 2011, 50, 7842-7846
35. Shaikh, R. R.; Mazzanti, A.; Petrini, M.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8707-8710
36. Brown, A. R.; Kuo, W.-H.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 9286-9288
37. Review: Emer, E.; Sinisi, R.; Capdevilla, M. G.; Petruzziello, D.; DeVincentiis, F.; Cozzi, P. G. Eur. J. Org. Chem. 2011, 647-666
38. Gómez-Bengoa, E.; Landa, A.; Lizarraga, A.; Mielgo, A.; Oiarbide, M.; Palomo, C. Chem. Sci. 2011, 2, 353-357
39. Elucidation of structure A versus B was made on the basis of NMR analysis (chemical shift and multiplicity) as illustrated in the Supporting Information. Isolable ammonium salts obtained from halides of type 2 and some selected tertiary amines and pyridines have recently been reported: Baidya, M.; Remennikov, G. Y.; Mayer, P.; Mayr, H. Chem.-Eur. J. 2010, 16, 1365-1371
40. Healey, B. Eur. J. Org. Chem. 2009, 1477-1489
41. Takeishi, K.; Sugishima, K.; Sasaki, K.; Tanaka, K. Chem.-Eur. J. 2004, 10, 5681-5688
42. Kai, K.; Takeuchi, J.; Kataoka, T.; Yokoyama, M.; Watanabe, N. Tetrahedron 2008, 6760-6769
43. Palomo, C.; Landa, A.; Mielgo, A.; Oiarbide, M.; Puente, A.; Vera, S. Angew. Chem., Int. Ed. 2007, 46, 8431-8435
44. Xiao, X.; Antony, S.; Kohlhagen, G.; Pommierb, Y.; Cushman, M. Bioorg. Med. Chem. 2004, 12, 5147-5160
45. Shi, M.; Li, C.-Q.; Jiang, J.-K. Molecules 2002, 7, 721-733
46. Das, B.; Banerjee, J.; Ravindranath, N. Tetrahedron 2004, 60, 8357-8361
47. Breton, G. W. J. Org. Chem. 1997, 62, 8952-8954
48. Kar, A.; Argade, N. P. Tetrahedron 2003, 59, 2991-2998