Chiral recyclable Cu(II)-catalysts in nitroaldol reaction of aldehydes with various nitroalkanes and its application in the synthesis of a valuable drug (R)-isoproterenol

Applied Catalysis A: General

Volumn 459, Issue , 2013, Pages 97-105

  Das, Anjan ^a   Kureshy, Rukhsana I ^a   Prathap, K Jeya ^b   Choudhary, Manoj K ^a   Rao, Ganga V S ^a   Khan, Noor Ul H ^a   Abdi, Sayed H R ^a   Bajaj, Hari C ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Nitroalcohols; (R) isoproterenol; Asymmetric catalysis; Asymmetric nitroaldol reaction; Copper(II) H4 salen complexes; Dimeric macrocyclic salen

Indexed keywords

ASYMMETRIC CATALYSIS; ISOPROTERENOL; MACROCYCLICS; NITROALCOHOLS; NITROALDOL; SALEN COMPLEX;

ALDEHYDES; CATALYSTS; COPPER; LIGANDS; PARAFFINS;

COPPER COMPOUNDS;

EID: 84877670517     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2013.03.032     Document Type: Article

References (61)

1. C. Palomo, M. Oiarbide, and A. Laso Eur J. Org. Chem. 256 2007 1 2574
2. L.C.R. Henry Hebd. Seances Acad. Sci. 120 1895 1265
3. E.J. Corey, and F.U. Zhang Angew. Chem. Int. Ed. 38 1999 1931 1933
4. K.Y. Spangler, and C. Wolf Org. Lett. 11 2009 4724 4727
5. M. Bandini, F. Piccinelli, S. Tommasi, A. Umani-Ronchi, and C. Ventrici Chem. Commun. 2007 616 618
6. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley-VCH New York
7. M. Yamaguchi, T. Shiraishi, and M. Hirama J. Org. Chem. 61 1996 3520 3530
8. M. Yamaguchi, Y. Igarashi, R.S. Reddy, T. Shiraishi, and M. Hirama Tetrahedron 53 1997 11223 11236
9. R. Breslow Science 218 1982 532 537
10. A.J. Kirby Angew. Chem. Int. Ed. Engl. 35 1996 707 724
11. J. Park, K. Lang, K.A. Abboud, and S. Hong J. Am. Chem. Soc. 130 2008 16484 16485
12. B.M. Choudary, K.V.S. Ranganath, U. Pal, M.L. Kantam, and B. Sreedhar J. Am. Chem. Soc. 127 2005 13167 13171
13. B.M. Trost, and V.S.C. Yeh Angew. Chem. 114 2002 889 891
14. B.M. Trost, V.S.C. Yeh, H. Ito, and N. Bremeyer Org. Lett. 4 2002 2621 2623
15. A. Bulut, A. Aslan, and Ö. Dogan J. Org. Chem. 73 2008 7373 7375
16. V.J. Mayani, S.H.R. Abdi, R.I. Kureshy, N.H. Khan, A. Das, and H.C. Bajaj J. Org. Chem. 75 2010 6191 6195
17. A. Noole, K. Lippur, A. Metsala, M. Lopp, and T. Kanger J. Org. Chem. 75 2010 1313 1316
18. M. Steurer, and C. Bolm J. Org. Chem. 75 2010 3301 3310
19. G. Blay, V. Hernández-Olmos, and J.R. Pedro Chem. Commun. 2008 4840 4842
20. T. Arai, M. Watanabe, and A. Yanagisawa Org. Lett. 9 2007 3595 3597
21. R. Kowalczyk, and J. Skarzewski Tetrahedron: Asymmetry 20 2009 2467 2673
22. N. Sanjeevkumar, and M. Periasamy Tetrahedron: Asymmetry 20 2009 1842 1847
23. S. Jammi, M.A. Ali, S. Sakthivel, L. Rout, and T. Punniyamurthy Chem. Asian J. 4 2008 314 320
24. S. Jammi, P. Saha, S. Sanyashi, and T. Punniyamurthy Tetrahedron 64 2008 11724 11731
25. B. Quin, X. Xiao, X. Liu, J. Huang, Y. Wen, and X. Feng J. Org. Chem. 72 2007 9323 9328
26. M. Breuning, D. Hein, M. Steiner, V.H. Gessner, and C. Strohmann Chem. Eur. J. 15 2009 12764 12769
27. M. Bandini, S. Cabiddu, E. Cadoni, P. Olivelli, R. Sinisi, A. Umani-Ronchi, and M. Usai Chirality 21 2009 239 244
28. I. Panov, P. Drabina, Z. Padlková, P. Šimůnek, and M. Sedlák J. Org. Chem. 76 2011 4787 4793
29. Y. Zhou, J. Dong, F. Zhang, and Y. Gong J. Org. Chem. 76 2011 588 600
30. M. Zielińska-Błajet, and J. Skarzewski Tetrahedron: Asymmetry 20 2009 1992 1998
31. R. Boobalan, G.-H. Lee, and C. Chena Adv. Synth. Catal. 354 2012 2511 2520
32. R.I. Kureshy, B. Dangi, A. Das, N.H. Khan, S.H.R. Abdi, and H.C. Bajaj Appl. Catal. A: Gen. 439-440 2012 74 79
33. R. Kowalczyk, Ł. Sidorowicz, and J. Skarzewski Tetrahedron: Asymmetry 18 2007 2581 2586
34. H. Sasai, T. Suzuki, S. Arai, T. Arai, and M. Shibasaki J. Am. Chem. Soc. 114 1992 4418 4420
35. A.P. Bhatt, K. Pathak, R.V. Jasra, R.I. Kureshy, N.H. Khan, and S.H.R. Abdi J. Mol. Catal. A: Chem. 244 2006 110 117
36. H. Sasai, M. Hiroi, Y.M.A. Yamada, and M. Shibasaki Tetrahedron Lett. 38 1997 6031 6034
37. M. Shibasaki, and H. Sasai Pure Appl. Chem. 68 1996 523 530
38. T. Arai, Y.M.A. Yamada, N. Yamamoto, H. Sasai, and M. Shibasaki Chem. Eur. J. 2 1996 1368 1372
39. M. Shibasaki, and N. Yoshikawa Chem. Rev. 102 2002 2187 2210
40. H. Sasai, S. Watanabe, T. Suzuki, and M. Shibasaki Org. Synth. 10 2004 571 577
41. T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skranc, D. Mink, and H. Griengl Angew. Chem. 118 2006 3532 3535
42. D.A. Evans, D. Seidel, M. Rueping, H.W. Lam, J.T. Shaw, and C.W. Downey J. Am. Chem. Soc. 125 2003 12692 12693
43. D.-M. Du, S.-F. Lu, T. Fang, and J. Xu J. Org. Chem. 70 2005 3712 3715
44. G. Blay, E. Climent, I. Fernández, V. Hernández-Olmos, and J.R. Pedro Tetrahedron: Asymmetry 17 2006 2046 2049
45. S. Liu, and C. Wolf Org. Lett. 10 2008 1831 1834
46. H.Y. Kim, and K. Oh Org. Lett. 11 2009 5682 5685
47. M. Çolak, T. Aral, H. Hoşgören, and N. Demirel Tetrahedron: Asymmetry 18 2007 1129 1133
48. Y. Zhang, L. Xiang, Q. Wang, X.-F. Duan, and G. Zi Inorg. Chim. Acta 361 2008 1246 1254
49. C. Palomo, M. Oiarbide, and A. Mielgo Angew. Chem. Int. Ed. 43 2004 5442 5444
50. T.M. Suzuki, M. Yamamoto, K. Fukumoto, Y. Akimoto, and K. Yano J. Catal. 251 2007 249 257
51. Y. Xiong, F. Wang, X. Huang, Y. Wen, and X. Feng Chem. Eur. J. 13 2007 829 833
52. R.I. Kureshy, A. Das, N.H. Khan, S.H.R. Abdi, and H.C. Bajaj ACS Catal. 1 2011 1529 1535
53. W. Brooks, C.H. Wesley, and Conrad Comput. Med. 59 2009 339 343
54. R. Vilskersts, E. Liepinsh, J. Kuka, H. Cirule, M. Veveris, I. Kalvinsh, and M. Dambrova Cardiovasc. Drug Ther. 23 2009 281 288
55. W. Jin, X. Li, and B. Wan J. Org. Chem. 76 2011 484 491
56. J.-J. Jianga, and M. Shi Tetrahedron: Asymmetry 18 2007 1376 1382
57. E.C. Constable, G. Zhang, C.E. Housecroft, M. Neuburger, S. Schaffner, and W. Woggon New J. Chem. 33 2009 1064 1069
58. P. Kumar, R.K. Upadhyay, and R.K. Pandey Tetrahedron: Asymmetry 15 2004 3955 3959
59. G. Blay, V. Hernández-Olmos, and J.R. Pedro Tetrahedron: Asymmetry 21 2010 578 581
60. E.J. Corey, and J.O. Link Tetrahedron Lett. 31 1990 601 604
61. R.I. Kureshy, K.J. Prathap, M. Kumar, P.K. Bera, N.H. Khan, S.H.R. Abdi, and H.C. Bajaj Tetrahedron 67 2011 8300 8307