Enantioselective Michael reaction of β-keto esters organocatalyzed by recoverable Cinchona-derived dimeric ammonium salts

Tetrahedron Asymmetry

Volumn 20, Issue 23, 2009, Pages 2651-2654

  Tarí, Silvia ^a   Chinchilla, Rafael ^a   Nájera, Carmen ^a  

^a Departamento de Química Orgánica   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; BETA KETO ESTER DERIVATIVE; CINCHONIDINE; ESTER DERIVATIVE; QUININE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CINCHONA; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 76449115669     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.11.007     Document Type: Article

References (44)

1. Review:. Cozzi P.G., Hilgraf R., and Zimmermann N. Eur. J. Org. Chem. (2007) 5969-5994
2. Perlmutter P. Conjugate Addition in Organic Synthesis (1992), Pergamon, Oxford
3. Reviews:. Jha S.C., and Joshi N.N. Arkivoc vii (2002) 167-196
4. Christoffers J., and Baro A. Angew. Chem., Int. Ed. 42 (2003) 1688-1690
5. Recent examples:. Nakajima M., Yamamoto S., Yamaguchi Y., Nakamura S., and Hashimoto S. Tetrahedron 59 (2003) 7307-7313
6. Kumaraswamy G., Jena N., Sastry M.N.V., Padmaja M., and Markondaiah B. Adv. Synth. Catal. 347 (2005) 867-871
7. Hamashima Y., Hotta D., Umebayashi N., Tsuchiya Y., Suzuki T., and Sodeoka M. Adv. Synth. Catal. 347 (2005) 1576-1586
8. Ogawa C., Kizu K., Shimizu H., Takeuchi M., and Kobayashi S. Chem. Asian J. 1-2 (2006) 121-124
9. Berkessel A., and Gröger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis (2005), Wiley-VCH, Weinheim
10. In: Dalko P.I. (Ed). Enantioselective Organocatalysis: Reactions and Experimental Procedures (2007), Wiley-VCH, Weinheim
11. General reviews:. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 40 (2001) 3726-3748
12. Seayad J., and List B. Org. Biomol. Chem. 3 (2005) 719-724
13. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
14. Reviews:. Almasi D., Alonso D.A., and Nájera C. Tetrahedron: Asymmetry 18 (2007) 299-365
15. Vicario J.L., Badía D., and Carrillo L. Synthesis (2007) 2065-2092
16. Tsogoeva S.B. Eur. J. Org. Chem. (2007) 1701-1716
17. Långström B., and Bergson G. Acta Chem. Scand. (1973) 3118-3119
18. Wynberg H., and Helder R. Tetrahedron Lett. (1975) 4057-4060
19. Hermann K., and Wynberg H. J. Org. Chem. 44 (1979) 2238-2244
20. Sera A., Takagi K., Katayama H., and Yamada H. J. Org. Chem. 53 (1988) 1157-1161
21. Szöllösi G., and Bartók M. Chirality 13 (2001) 614-618
22. Wu F., Li H., Hong R., and Deng L. Angew. Chem., Int. Ed. 45 (2006) 947-950
23. Wu F., Hong R., Khan J., Liu X., and Deng L. Angew. Chem., Int. Ed. 45 (2006) 4301-4305
24. Rigby C.L., and Dixon D.J. Chem. Commun. (2008) 3798-3800
25. Hashimoto T., and Maruoka K. Chem. Rev. 107 (2007) 5656-5682
26. In: Maruoka K. (Ed). Asymmetric Phase-Transfer Catalysis (2008), Wiley-VCH, Weinheim
27. Maruoka K. Org. Process Res. Dev. 12 (2008) 679-697
28. Díez-Barra E., de la Hoz A., Merino S., Rodríguez A., and Sánchez-Verdú P. Tetrahedron 54 (1998) 1835-1844
29. Ooi T., Miki T., Taniguchi M., Shiraishi M., Takeuchi M., and Maruoka K. Angew. Chem., Int. Ed. 42 (2003) 3796-3798
30. Chinchilla R., Mazón P., and Nájera C. Tetrahedron: Asymmetry 13 (2002) 927-931
31. Chinchilla R., Mazón P., Nájera C., and Ortega F.J. Tetrahedron: Asymmetry 15 (2004) 2603-2607
32. Chinchilla R., Mazón P., Nájera C., Ortega F.J., and Yus M. Arkivoc vi (2005) 222-232
33. Chinchilla R., Mazón P., and Nájera C. Tetrahedron: Asymmetry 11 (2000) 3277-3281
34. Chinchilla R., Mazón P., and Nájera C. Molecules 9 (2004) 349-364
35. Chinchilla R., Mazón P., and Nájera C. Adv. Synth. Catal. 346 (2004) 1186-1194
36. Chinchilla R., Nájera C., and Ortega F.J. Tetrahedron: Asymmetry 19 (2008) 265-268
37. Chinchilla R., Nájera C., Ortega F.J., and Tarí S. Tetrahedron: Asymmetry 20 (2009) 2279-2286
38. Moss T.A., Fenwick D.R., and Dixon D.J. J. Am. Chem. Soc. 130 (2008) 10076-10077
39. Enantioselectivities were determined by chiral HPLC using Chiralcel OJ (5aa,ba,ca,da,ea) and Chiralcel OD-H (5ab,db,ac,ad,ae) columns and n-hexane/2-propanol mixtures as eluent. Reference racemic samples of adducts 5 were prepared by performing the enantioselective Michael reaction in the absence of chiral ammonium salt.
40. Absolute configuration for adducts 5aa,ba,ac (Ref. 4a), 5ab (Ref. 10b) and 5ae (Ref. 10c) was determined according to the described order of elution of their enantiomers in chiral HPLC. The absolute configuration of other adducts was assigned by analogy.
41. C 157.9, 147.4, 145.4, 143.8, 138.0, 137.9, 132.9, 132.7, 131.3, 125.6, 122.0, 118.8, 116.7, 101.8, 65.8, 58.9, 56.9, 55.5, 48.0, 46.9, 36.4, 26.8, 22.7, 17.1.
42. 1H NMR (300 MHz).
43. +-tBu, 14), 131 (100).
44. House H.O., and Hudson C.B. J. Org. Chem. 35 (1970) 647-651