Highly enantioselective proline-catalysed direct aldol reaction of chloroacetone and aromatic aldehydes

Chemistry - A European Journal

Volumn 18, Issue 17, 2012, Pages 5188-5190

  Martínez Castañeda, Ángel ^a   Poladura, Belén ^a   Rodríguez Solla, Humberto ^a   Concellón, Carmen ^a   Del Amo, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

aldol reaction; guanidinium salts; organocatalysis; proline

Indexed keywords

ALDOL REACTIONS; AROMATIC ALDEHYDE; DIASTEREO- AND ENANTIOSELECTIVITY; DIRECT ALDOL REACTION; ENANTIOSELECTIVE; GUANIDINIUM; MECHANICAL STIRRING; ORGANOCATALYSIS; PROLINE; TEST TUBE;

ALDEHYDES; AROMATIC COMPOUNDS; CATALYSIS; CONDENSATION REACTIONS; ENANTIOSELECTIVITY; REACTION KINETICS;

AMINO ACIDS;

ACETONE; ALDEHYDE; CHLOROACETONE; DRUG DERIVATIVE; GUANIDINE; PROLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETONE; ALDEHYDES; CATALYSIS; GUANIDINE; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 84859884257     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103667     Document Type: Article

References (38)

1. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395.
2. P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840
3. Angew. Chem. Int. Ed. 2001, 40, 3726
4. B. List, Synlett 2001, 1675
5. B. List, Tetrahedron 2002, 58, 5573
6. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248
7. Angew. Chem. Int. Ed. 2004, 43, 5138
8. W. Notz, F. Tanaka, C. F. Barbas, Acc. Chem. Res. 2004, 37, 580
9. J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719
10. B. List, Chem. Commun. 2006, 819
11. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79
12. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471
13. A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716
14. Angew. Chem. Int. Ed. 2008, 47, 4638
15. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232
16. Angew. Chem. Int. Ed. 2008, 47, 6138
17. C. F. Barbas, Angew. Chem. 2008, 120, 44
18. Angew. Chem. Int. Ed. 2008, 47, 42
19. Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745
20. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178
21. X. Liu, L. Lin, X. Feng, Chem. Commun. 2009, 6145.
22. A. Martínez-Castañeda, B. Poladura, H. Rodríguez- Solla, C. Concellón, V. del Amo, Org. Lett. 2011, 13, 3032.
23. Y. Zhou, Z. Shan, J. Org. Chem. 2006, 71, 9510
24. Ö. Reis, S. Eymur, B. Reis, A. S. Demir, Chem. Commun. 2009, 1088
25. X. Companyó, G. Valero, L. Crovetto, A. Moyano, R. Rios, Chem. Eur. J. 2009, 15, 6564
26. N. El-Hamdouni, X. Companyó, R. Rios, A. Moyano, Chem. Eur. J. 2010, 16, 1142
27. G. Ma, A. Bartoszewicz, I. Ibrahem, A. Córdova, Adv. Synth. Catal. 2011, 353, 3114.
28. The aldol reaction between chloroacetone and aromatic aldehydes has only been performed by using 50 mol % proline in ionic liquids as the solvent. Only two examples are reported. Enantiomeric excesses of the desired chlorohydrins are not described:, T. Kitazume, Z. Jiang, K. Kasai, Y. Mihara, M. Suzuki, J. Fluorine Chem. 2003, 121, 205.
29. K. Shibatomi, Synthesis 2010, 2679.
30. L. He, Z. Tang, L. F. Cun, A. Q. Mi, Y. Z. Jiang, L.- Z. Gong, Tetrahedron 2006, 62, 346.
31. A. Russo, G. Botta, A. Lattanzi, Tetrahedron 2007, 63, 11886.
32. G. Guillena, M. d. C. Hita, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 1272
33. G. Guillena, M. d. C. Hita, C. Nájera, S. F. Viózquez, J. Org. Chem. 2008, 73, 5933.
34. X.-Y. Xu, Y.-Z. Wang, L.-Z. Gong, Org. Lett. 2007, 9, 4247.
35. r=8.8 (major), 10.9 min (minor)), with that previously reported in the literature (reference [9a]) authenticates its absolute configuration.
36. S. Arai, Y. Shirai, T. Ishida, T. Shioiri, Tetrahedron 1999, 55, 6375
37. C. Peppe, R. P. das Chagas, Synlett 2006, 0605.
38. M. E. Krafft, S. J. R. Twiddle, J. W. Cran, Tetrahedron Lett. 2011, 52, 1277.