Per-6-amino-β-cyclodextrin as a reusable promoter and chiral host for enantioselective henry reaction

Organic Letters

Volumn 12, Issue 18, 2010, Pages 4070-4073

  Kanagaraj, Kuppusamy ^a   Suresh, Palaniswamy ^a   Pitchumani, Kasi ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BETA CYCLODEXTRIN DERIVATIVE; PER 6 AMINO BETA CYCLODEXTRIN; PER-6-AMINO-BETA-CYCLODEXTRIN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; BETA-CYCLODEXTRINS; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77956593053     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101658n     Document Type: Article

References (56)

1. Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2024
2. Ojima, I., Ed. Catalytic Asymmetric Synthesis, 3rd Ed.; John Wiley & Sons: Hoboken, NJ, 2010.
3. Hawkins, J. M.; Watson, T. J. N. Angew. Chem., Int. Ed. 2004, 43, 3224
4. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999.
5. Sharma, K. K.; Biradar, A. V.; Asefa, T. ChemCatChem 2010, 2, 61
6. De Vos, D. E.; Vankelecom, I. F. J.; Jacobs, P. A. Chiral Catalysts Immobilization and Recycling; Wiley-VCH: Weinheim, 2000.
7. Burk, M. J.; Gerlach, A.; Semmeril, D. J. Org. Chem. 2000, 65, 8933
8. Palomo, C.; Mielgo, A. Angew. Chem. 2006, 118, 8042
9. Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876
10. Jammi, S.; Punniyamurthy, T. Eur. J. Inorg. Chem. 2009, 2508
11. Mora, M.; Jimenez-Sanchidrian, C.; Urbano, F. J.; Ruiz, J. R. Catal. Lett. 2010, 134, 131
12. Reviews
13. Marqus-Lopez, E.; Merino, P.; Tejero, T.; Herrera, R. P. Eur. J. Org. Chem. 2009, 2401
14. Zhang, B.; Cai, L.; Song, H.; Wang, Z.; He, Z. Adv. Synth. Catal. 2010, 352, 97
15. Baleizao, C.; Garcia, H. Chem. Rev. 2006, 106, 3987
16. Shi, L.; Wang, X.; Sandoval, C. A.; Li, M.; Qi, Q.; Li, Z.; Ding, K. Angew. Chem. 2006, 118, 421
17. For some recent examples of enantioselective Henry reactions, see
18. Park, J.; Lang, K.; Abboud, K. A.; Hong, S. J. Am. Chem. Soc. 2008, 130, 16484
19. Blidi, L. E.; Assaf, Z.; Bres, F. C.; Veschambre, H.; Thery, V.
20. Bolte, J.; Lemaire, M. ChemCatChem. 2009, 1, 463
21. Wang, J.-L.; Li, X.; Xie, H.-Y.; Liu, B.-K.; Lin, X.-F. J. Biotechnol. 2010, 145, 240
22. Ingalsbe, M. L.; St. Denis, J. D.; Gleason, J. L.; Savage, G. P.; Priefer, R. Synthesis 2010, 1, 98
23. Breuning, M.; Hein, D.; Steiner, M.; Gessner, V. H.; Strohmann, C. Chem. - Eur. J. 2009, 15, 12764
24. Noole, A.; Lippur, K.; Metsala, A.; Lopp, M.; Kanger, T. J. Org. Chem. 2010, 75, 1313
25. Takahashi, K. Chem. Rev. 1998, 98, 2013
26. Sakuraba, H.; Maekawa, H. J. Inclusion Phenom. Macrocyclic Chem. 2006, 54, 41
27. Bhosale, S. V.; Bhosale, S. V. Mini-Rev. Org. Chem. 2007, 4, 231
28. Harano, K.; Kiyonaga, H.; Hissano, T. Tetrahedron Lett. 1991, 32, 7557
29. Krishnaveni, N. S.; Surendra, K.; Rao, K. R. Chem. Commun. 2005, 669
30. Surendra, K.; Krishnaveni, N. S.; Sridhar, R.; Rao, K. R. Tetrahedron Lett. 2006, 47, 2125
31. Tang, W.; Tang, J.; Ng, S. C.; Chan, H. S. O. J. Inclusion Phenom. Macrocyclic Chem. 2006, 56, 287
32. Dignam, C. F.; Randall, L. A.; Blacken, R. D.; Cunningham, P. R.; Lester, S.-K. G.; Brown, M. J.; French, S. C.; Aniagyei, S. E.; Wenzel, T. J. Tetrahedron: Asymmetry 2006, 17, 1199
33. McCracken, P. G.; Ferguson, C. G.; Vizitiu, D.; Walkinshaw, C. S.; Wang, Y.; Thatcher, G. R. J. J. Chem. Soc., Perkin Trans. 2 1999, 911
34. Kitae, T.; Nakayama, T.; Kano, K. J. Chem. Soc., Perkin Trans. 2 1998, 207
35. Meo, P. L.; DAnna, F.; Gruttadauria, M.; Riela, S.; Noto, R. Tetrahedron 2009, 65, 10413
36. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423
37. Groger, H.; Willken, J. Angew. Chem., Int. Ed. 2001, 40, 529
38. Suresh, P.; Pitchumani, K. J. Org. Chem. 2008, 73, 9121
39. Suresh, P.; Pitchumani, K. Tetrahedron: Asymmetry 2008, 19, 2037
40. Kanagaraj, K.; Pitchumani, K. Tetrahedron Lett. 2010, 51, 3312
41. Suresh, P.; Azath, I. A.; Pitchumani, K. Sens. Actuators B 2010, 146, 273
42. Petter, R. C.; Salek, J. S.; Sikorski, C. T.; Kumaravel, G.; Lin, F.-T. J. Am. Chem. Soc. 1990, 112, 3860
43. Tang, W.; Ng, S.-C. Nature Protocols 2008, 3, 691
44. Lai, G.; Wang, S.; Wang, Z. Tetrahedron: Asymmetry 2008, 19, 1813
45. Selvakumar, S.; Sivasankaran, D.; Singh, V. K. Org. Biomol. Chem. 2009, 7, 3156
46. Sasai, H.; Hiroi, M.; Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 6031
47. Liu, S.; Wolf, C. Org. Lett. 2008, 10, 1831
48. For a syn-selective direct nitroaldol reaction, see
49. Arai, T.; Takashita, R.; Endo, Y.; Watanabe, M.; Yanagisawa, A. J. Org. Chem. 2008, 73, 4903
50. Toussaint, A.; Pfaltz, A. Eur. J. Org. Chem. 2008, 4591
51. Kowalczyk, R.; Skarzewski, J. Tetrahedron: Asymmetry 2009, 20, 2467
52. For an anti-selective direct nitroaldol reaction, see
53. Blay, G.; Domingo, L. R.; Hernández-Olmos, V.; Pedro, J. R. Chem. - Eur. J. 2008, 14, 4725
54. Kim, H. Y.; Oh, K. Org. Lett. 2009, 11, 5682
55. Risgaard, T.; Gothelf, K. V.; Jørgensen, K. A. Org. Biomol. Chem. 2003, 1, 153
56. Hamelin, B.; Jullien, L.; Guillo, F.; Lehn, J.-M.; Jardy, A.; De Robertis, L.; Driguez, H. J. Phys. Chem. 1995, 99, 17877