Asymmetric henry reaction catalyzed by a chiral Cu(II) complex: A facile enantioselective synthesis of (S)-2-nitro-1-arylethanols

Tetrahedron Asymmetry

Volumn 22, Issue 5, 2011, Pages 530-535

  Reddy, Basi V Subba ^a   Reddy, Sankham Madhusudana ^a   Manisha, Swain ^a   Madan, Chinnala ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1 NAPHTHYL) 2 NITROETHANOL; 1 (2 NITROPHENYL) 2 NITROETHANOL; 1 (3,4 DICHLOROPHENYL) 2 NITROETHANOL; 1 (3,4 DIMETHOXYPHENYL) 2 NITROETHANOL; 1 (4 BROMOPHENYL) 2 NITROETHANOL; 1 (4 CHLOROPHENYL) 2 NITROETHANOL; 1 (4 FLUOROPHENYL) 2 NITROETHANOL; 1 (4 IODOPHENYL) 2 NITROETHANOL; 1 (4 METHOXYPHENYL) 2 NITROETHANOL; 1 (4 NITROPHENYL) 2 NITROETHANOL; 1 NITROPENTAN 2 OL; 1 PHENYL 2 NITRO ETHANOL; 2 (DIPHENYLMETHANOL) 1 (2 PYRIDYLMETHYL)PYRROLIDINE; ALCOHOL; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; COPPER COMPLEX; NITROGEN; NITROGEN DERIVATIVE; PYRIDINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYSIS; CHIRALITY; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 79955437696     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.02.019     Document Type: Article

References (62)

1. R.R. Ruffolo Jr. Tetrahedron 47 1991 9953
2. S.C. Stinson Chem. Eng. News 70 1992 46
3. K. Nakamura, Y. Kawai, S. Oka, and A. Ohno Bull. Chem. Soc. Jpn. 62 1989 875
4. L.W. Weinstock, D.M. Mulvey, and R. Tull J. Org. Chem. 41 1976 3121
5. J. Trofast, K. Osterberg, B.L. Kallstrom, and B. Waldeck Chirality 3 1991 443
6. L. Lohse, and C. Spodlin Org. Process Res. Dev. 1 1997 247
7. H.J. Roth, and A. Klemann Pharmaceutical Chemistry Drug Synthesis Vol. 1 1988 Ellis Wood UK p 144
8. J.D. Morrison, and J.W. Scott Asymmetric Synthesis 1984 Academic Press New York pp 2-4
9. D.J. Agar, I. Prakash, and D.R. Schaad Chem. Rev. 96 1996 835
10. F.A. Luzzio Tetrahedron 57 2001 915
11. C. Palomo, M. Oiarbide, and A. Laso Eur. J. Org. Chem. 16 2007 2561
12. B.M. Trost, V.S.C. Yeh, H. Ito, and N. Bremeyer Org. Lett. 4 2002 2621
13. H. Sasai, T. Suzuki, N. Itoh, S. Arai, and M. Shibasaki Tetrahedron Lett. 34 1983 2657
14. H. Sasai, N. Itoh, T. Suzuki, and M. Shibasaki Tetrahedron Lett. 34 1983 855
15. H. Sasai, T. Yamada, Y.M.A. Suzuki, and M. Shibasaki Tetrahedron 50 1994 12313
16. D.A. Lednicer, and L.A. Mitscher The Organic Chemistry of Drug Synthesis 1975 John Wiley and Sons New York
17. P.M. Koskinenand, and M.P. Koskinen Synthesis 1998 1075
18. S.-F. Lu, B. Herbert, G. Haufe, K.W. Laue, W.L. Padgett, O. Oshunleti, J.W. Daly, and K.L. Kirk J. Med. Chem. 43 2000 1611
19. P.A. Procopiou, G.E. Morton, M. Todd, and G. Webb Tetrahedron: Asymmetry 2001 2005 12
20. J.S. Yadav, P.T. Reddy, S. Nanda, and A.B. Rao Tetrahedron: Asymmetry 12 2001 63
21. A. Kamal, A.A. Shaik, M. Sandbhor, and M.S. Malik Tetrahedron: Asymmetry 15 2004 3939
22. L. Henry C.R. Hebd. Acad. Sci. 120 1895 1265
23. G. Rosini B.M. Trost, C.H. Heathcock, Comprehensive Organic Synthesis Vol. 2 1991 Pergamon Oxford 321
24. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley VCH, New York Chapter 3, p 30
25. H. Sasai, T. Suzuki, S. Arai, T. Arai, and M. Shibasaki J. Am. Chem. Soc. 114 1992 4418
26. H. Sasai, T. Suzuki, N. Itoh, and M. Shibasaki Tetrahedron Lett. 34 1993 851
27. H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura, and M. Shibasaki J. Am. Chem. Soc. 115 1993 10372
28. H. Sasai, Y.M.A. Yamada, T. Suzuki, and M. Shibasaki Tetrahedron 50 1994 12313
29. H. Sasai, W.-S. Kim, T. Suzuki, M. Shibasaki, M. Mitsuda, J. Hasegawa, and T. Ohashi Tetrahedron Lett. 35 1994 6123
30. H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, and M. Shibasaki J. Org. Chem. 60 1995 7388
31. K. Iseki, S. Oishi, H. Sasai, and M. Shibasaki Tetrahedron Lett. 37 1996 9081
32. M. Shibasaki, H. Sasai, and T. Arai Angew. Chem., Int. Ed. 36 1997 1236
33. M. Shibasaki, and N. Yoshikawa Chem. Rev. 102 2002 2187
34. C. Christensen, K. Juhl, and K.A. Jørgensen Chem. Commun. 2001 2222
35. C. Christensen, K. Juhl, R.G. Hazell, and K.A. Jørgensen J. Org. Chem. 67 2002 4875
36. For organocatalysts see: Y. Sohtome, Y. Hashimoto, and K. Nagasawa Adv. Synth. Catal. 347 2005 1643
37. Y. Sohtome, Y. Hashimoto, and K. Nagasawa Eur. J. Org. Chem. 2006 2894
38. T. Marcelli, R.N.S. van der Haas, J.H. van Maarseveen, and H. Hiemstra Angew. Chem., Int. Ed. 45 2006 929
39. T. arcelli, R.N.S. van der Haas, J.H. van Maarseveen, and H. Hiemstra Angew. Chem., Int. Ed. 45 2006 7496
40. M.S. Taylor, and E.N. Jacobsen Angew. Chem., Int. Ed. 45 2006 1520
41. S.J. Connon Chem. Eur. J. 12 2006 5418
42. P.M. Pihko Angew. Chem., Int. Ed. 43 2004 2062
43. P.R. Schreiner Chem. Soc. Rev. 32 2003 289
44. H. Li, B. Wang, and L. Deng J. Am. Chem. Soc. 128 2006 732
45. K. Takada, N. Takemura, K. Cho, Y. Sohtome, and K. Nagasawa Tetrahedron Lett. 49 2008 1623
46. For reviews on the asymmetric Henry reaction see: C. Palomo, M. Oiarbide, and A. Laso Eur. J. Org. Chem. 2007 2561
47. J. Boruwa, N. Gogoi, P.P. Saikia, and N.C. Barua Tetrahedron: Asymmetry 17 2006 3315
48. C. Palomo, M. Oiarbide, and A. Mielgo Angew. Chem., Int. Ed. 43 2004 5442
49. E. Marqués-López, P. Merino, T. Tejero, and R.P. Herrera Eur. J. Org. Chem. 15 2009 2401
50. S.C. Stinson Chem. Eng. News 78 2000 59
51. M. Mahmoudin Biocatalysis Biotransformation 18 2000 105
52. G. Blay, E. Climent, I. Fernandez, V. Hernandez-Olmos, and J.R. Pedro Tetrahedron: Asymmetry 17 2006 2046
53. Y.X. Zhang, D.M. Du, X. Chen, S.F. Lu, and W.T. Hua Tetrahedron: Asymmetry 15 2004 177
54. H. Maheswaran, K.L. Prasanth, G.G. Krishna, K.R. Kumar, B. Sridhar, and M.L. Kantam Chem. Commun. 2006 4066
55. G. Blay, E. Climent, I. Fernandez, H.V. Olmos, and J.R. Pedro Tetrahedron: Asymmetry 18 2007 1603
56. G. Lai, S. Wang, and Z. Wang Tetrahedron: Asymmetry 19 2008 1813
57. N.S. Kumar, and M. Periasamy Tetrahedron: Asymmetry 20 2009 1842
58. G. Blay, H.V. Olmos, and J.R. Pedro Tetrahedron: Asymmetry 21 2010 578
59. B.T. Cho, S.K. Kang, and S.H. Shin Tetrahedron: Asymmetry 13 2002 1209
60. G. Chelucci, M. Falorni, and G. Giacometli Tetrahedron: Asymmetry 11 1990 843
61. Y.X. Zhang, D.M. Du, X. Chen, S.F. Lu, and W. Ting Hua Tetrahedron: Asymmetry 15 2004 177
62. Y. Shen, X. Feng, Y. Li, G. Zhang, and Y. Jiang Eur. J. Org. Chem. 2004 129