Highly enantioselective Henry reaction catalyzed by a new chiral C2-symmetric N,N′-bis(isobornyl)ethylenediamine-copper complex

Tetrahedron Asymmetry

Volumn 20, Issue 16, 2009, Pages 1842-1847

  Sanjeevakumar, Nalluri ^a   Periasamy, Mariappan ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ALDEHYDE DERIVATIVE; COPPER COMPLEX; DIAMINE DERIVATIVE; DICHLOROMETHANE; ETHYLENEDIAMINE DERIVATIVE; LIGAND; NITROALKANE; NITROMETHANE;

ARTICLE; ASYMMETRIC CATALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; HENRY REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 69749097791     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.07.040     Document Type: Article

References (43)

1. Luzzio F.A. Tetrahedron 57 (2001) 915
2. Palomo C., Oiarbide M., and Laso A. Eur. J. Org. Chem. 16 (2007) 2561
3. Sasai H., Suzuki T., Arai S., and Shibasaki M. J. Am. Chem. Soc. 114 (1992) 4418
4. Christensen C., Juhl K., and Jørgensen K.A. Chem. Commun. (2001) 2222
5. Evans D.A., Seidel D., Rueping M., Lam H.W., Shaw J.T., and Downey C.D. J. Am. Chem. Soc. 125 (2003) 12692
6. Trost B.M., and Yeh V.S.C. Angew. Chem., Int. Ed. 41 (2002) 861
7. Palomo C., Oiarbide M., and Mielgo A. Angew. Chem., Int. Ed. 43 (2004) 5442
8. Kogami Y., Nakajima T., Ikeno T., and Yamada T. Synthesis (2004) 1947
9. Palomo C., Oiarbide M., and Laso A. Angew. Chem., Int. Ed. 44 (2005) 3881
10. Wolf C., and Liu S. Org. Lett. 9 (2008) 1831
11. Chinchilla R., Nájera C., and Sánchez-Agulló P. Tetrahedron: Asymmetry 5 (1994) 1393
12. Allingham M.T., Howard-Jones A., Murphy P.J., Thomas D., and Caulkett P. Tetrahedron Lett. 44 (2003) 8677
13. Sohtome Y., Hashimoto Y., and Nagasawa K. Adv. Synth. Catal. 347 (2005) 1643
14. Sohtome Y., Hashimoto Y., and Nagasawa K. Eur. J. Org. Chem. 13 (2006) 2894
15. Wamg H., Li B., and Deng L. J. Am. Chem. Soc. 128 (2006) 732
16. Lu S.-F., Du D.-M., Zhang S.-W., and Xu J. Tetrahedron: Asymmetry 15 (2004) 3433
17. Gan C., Lai G., Zang Z., Wang Z., and Zhou M.-M. Tetrahedron: Asymmetry 17 (2006) 725
18. Blay G., Climent E., Fernández I., Hernández-Olmos V., and Pedro J.R. Tetrahedron: Asymmetry 17 (2006) 2046
19. Choudary B.M., Ranganathan K.V.S., Pal U., Kantam M.L., and Sreedhar B. J. Am. Chem. Soc. 127 (2005) 13167
20. Bandini M., Piccinelli F., Tommasi S., Umani-Ronchi A., and Ventrici C. Chem. Commun. (2007) 616
21. Arai T., Watanab M., and Yanagisawa A. Org. Lett. 9 (2007) 3595
22. Ginotra S.K., and Singh V.K. Org. Biomol. Chem. 5 (2007) 3932
23. Jiang J.J., and Shi M. Tetrahedron: Asymmetry 18 (2007) 1376
24. Xiong Y., Wang F., Huang X., Wen Y., and Feng X. Chem. Eur. J. 13 (2007) 829
25. Arai T., Watanabe M., and Yanagisawa A. Org. Lett. 9 (2007) 3595
26. Blay G., Domingo L.R., Hernandez-Olmos V., and Pedro J.R. Chem. Eur. J. 14 (2008) 4725
27. Kowalczyk R., Sidorowicz L., and Skarżewski J. Tetrahedron: Asymmetry 19 (2009) 2310
28. Brues F., Kulhanek J., and Ruzicka A. Tetrahedron Lett. 50 (2009) 3042
29. Periasamy M., Reddy M.N., and Anwar S. Tetrahedron: Asymmetry 15 (2004) 1809
30. Padmaja M., and Periasamy M. Tetrahedron: Asymmetry 15 (2004) 2437
31. Satishkumar S., and Periasamy M. Tetrahedron: Asymmetry 17 (2006) 1116
32. Periasamy M., Devasagayaraj A., Satyanarayana N., and Narayana C. Synth. Commun. 19 (1989) 565
33. Ipaktschi J. Chem. Ber. 117 (1984) 856
34. Narayana C., and Periasamy M. Chem. Commun. (1987) 1857
35. Caselli A., Giovenzana G.B., Palmisano G., Sisti M., and Pilati T. Tetrahedron: Asymmetry 14 (2003) 1451
36. 2, Z = 2, 7136 reflections measured, 2705 unique (Rint = 0.0289) which were used in all calculations. The final wR(F2) was 0.0616 (CCDC NO.727196).
37. Trost B.M., Yeh V.S.C., Ito H., and Bremeyer N. Org. Lett. 4 (2002) 2621
38. Sasai H., Suzuki T., Itoh N., Arai S., and Shibasaki M. Tetrahedron Lett. 34 (1983) 2657
39. Sasai H., Itoh N., Suzuki T., and Shibasaki M. Tetrahedron Lett. 34 (1983) 855
40. Sasai H., Yamada T., Suzuki Y.M.A., and Shibasaki M. Tetrahedron 50 (1994) 12313
41. Lednicer D.A., and Mitscher L.A. The Organic Chemistry of Drug Synthesis (1975), John Wiley and Sons, New York
42. Koskinenand P.M., and Koskinen M.P. Synthesis (1998) 1075
43. Bulut A., Aslan A., and Dogan O. J. Org. Chem. 73 (2008) 7373