A general stereoselective enamine mediated alkylation of α-substituted aldehydes

Chemical Communications

Volumn 48, Issue 30, 2012, Pages 3614-3616

  Gualandi, Andrea ^a   Petruzziello, Diego ^a   Emer, Enrico ^a   Cozzi, Pier Giorgio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ENAMINE;

ALKYLATION; ARTICLE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84858387119     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc17482k     Document Type: Article

References (34)

1. J. Christoffers, A. Baro, Adv. Synth. Catal., 2005, 347, 1473-1482.
2. B. M. Trost, C. Jiang, Synthesis, 2006, 369-396.
3. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem., 2007, 5969-5994.
4. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem., Int. Ed., 2008, 47, 6138-6171.
5. M. Bella, T. Gasperi, Synthesis, 2009, 1583-1614.
6. C. Zhong, X. Shi, Eur. J. Org. Chem., 2010, 2999-3025.
7. Z. Shao, H. Zhang, Chem. Soc. Rev., 2009, 38, 2745-2755.
8. A.-N. Alba, M. Viciano, R. Ríos, ChemCatChem, 2009, 1, 437-439.
9. U.-H. Dolling, P. Davis, E. J. J. Grabowsky, J. Am. Chem. Soc., 1984, 106, 446-447.
10. K. Maruoka, T. Ooi, Chem. Rev., 2003, 103, 3013-3038.
11. Enantioselective Organocatalysis, ed. P. I. Dalko, Wiley-VCH, Weinheim, 2007.
12. T. Ooi, M. Takeuchi, M. Kamada, K. Maruoka, J. Am. Chem. Soc., 2000, 122, 5228-5229.
13. T. D. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton, D. W. C. MacMillan, Science, 2007, 316, 582-585.
14. D. A. Nicewicz, D. W. C. MacMillan, Science, 2008, 322, 77-80.
15. E. Gómez-Bengoa, A. Landa, A. Lizarraga, A. Mielgo, M. Oiarbide, C. Palomo, Chem. Sci., 2011, 2, 353-357.
16. A. R. Brown, W.-H. Kuo, E. N. Jacobsen, J. Am. Chem. Soc., 2010, 132, 9286-9287.
17. P. G. Cozzi, F. Benfatti, L. Zoli, Angew. Chem., Int. Ed., 2009, 48, 1313-1316.
18. L. Zhang, L. Cui, X. Li, S. Luo, J.-P. Cheng, Chem. Eur. J., 2010, 16, 2045-2049.
19. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem., Int. Ed., 2010, 49, 9685-9688.
20. S. Mukherjee, B. List, J. Am. Chem. Soc., 2007, 129, 11336-11337.
21. M. G. Capdevila, F. Benfatti, L. Zoli, M. Stenta, P. G. Cozzi, Chem. Eur. J., 2010, 16, 11237-11241.
22. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta, 2006, 39, 79-87.
23. A. Gualandi, E. Emer, M. Guiteras Capdevila, P. G. Cozzi, Angew. Chem., Int. Ed., 2011, 50, 7842-7844.
24. R. P. Sonawane, V. Jheengut, C. Rabalakos, R. Larouche-Gauthier, H. K. Scott, V. K. Aggarwal, Angew. Chem., Int. Ed., 2011, 50, 3760-3763.
25. S. H. McCooey, S. J. Connon, Org. Lett., 2007, 9, 599-602.
26. A. Lee, A. Michrowska, S. Sulzer-Mosse, B. List, Angew. Chem., Int. Ed., 2011, 50, 1707-1710.
27. P. Melchiorre, G. Bartoli, Synlett, 2008, 1759-1771.
28. Y.-C. Chen, Synlett, 2008, 1919-1930.
29. G. K. Prakash, F. Wang, C. Ni, J. Shen, R. Haiges, A. K. Yudin, T. Matthew, G. A. Olah, J. Am. Chem. Soc., 2011, 133, 9992-9995.
30. X. Tian, C. Cassani, Y. Liu, A. Moran, A. Urakawa, P. Galzerano, E. Arceo, P. Melchiorre, J. Am. Chem. Soc., 2011, 133, 17934-17941.
31. C. Liu, Q. Zhu, K. W. Huang, Y. Lu, Org. Lett., 2011, 13, 2638-2641.
32. L. Hintermann, M. Schmitz, U. Eglert, Angew. Chem., Int. Ed., 2007, 46, 5164-5167.
33. S. Karlsson, H.-E. Hçgberg, Synthesis, 2000, 1863-1867.
34. D. S. Im, C. S. Cheong, S. H. Lee, J. Mol. Catal. B: Enzym., 2003, 26, 131-143.