Recoverable PEG-supported copper catalyst for highly stereocontrolled nitroaldol condensation

Organic Letters

Volumn 9, Issue 11, 2007, Pages 2151-2153

  Bandini, Marco ^a   Benaglia, Maurizio ^b   Sinisi, Riccardo ^a   Tommasi, Simona ^a   Umani Ronchi, Achille ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34250666228     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070636w     Document Type: Article

References (39)

1. Henry, L. C. R. Hebd. Seances Acad. Sci. 1895, 120, 1265.
2. (a) Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1996.
3. (b) Luzzio, F. A. Tetrahedron 2001, 57, 915.
4. (b) Ono, N. In The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
5. (a) Palomo, C.; Oiarbide, M.; Mielgo, A. Angew. Chem., Int. Ed. 2004, 43, 5442.
6. (b) Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C. Tetrahedron: Asymmetry 2006, 17, 3315.
7. (c) Palomo, C.; Oiarbide, M.; Laso, A. DOI: 10.1002/ejoc.200700021.
8. For studies regarding stereoselective Henry reactions under heterogeneous conditions, see: (a) Choudary, B. M.; Ranganath, K. V. S.; Pal, U.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 13167.
9. (b) Bhatt, A. P.; Pathak, K.; Jasra, R. V.; Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R. J. Mol. Catal. A: Chem. 2006, 244, 110.
10. (c) Arai, T.; Watanabe, M.; Fujiwara, A.; Yokoyama, N.; Yanagisawa, A. Angew. Chem., Int. Ed. 2006, 45, 5978.
11. Trost, B. M. Science 1991, 254, 1471.
12. Melucci, M.; Barbarella, G.; Gazzano, M.; Cavallini, M.; Biscarini, F.; Bongini, A.; Piccinelli, F.; Monari, M.; Bandini, M.; Umani-Ronchi, A.; Biscarini, P. Chem.-Eur. J. 2006, 12, 7304.
13. (a) Albano, V. G.; Bandini, M.; Melucci, M.; Monari, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi. A. Adv. Synth. Catal. 2005, 347, 1502.
14. (b) Albano, V. G.; Bandini, M.; Barbarella, G.; Melucci, M.; Monari, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A. Chem.-Eur. J. 2006, 12, 667.
15. (c) Albano, V. G.; Bandini, M.; Monari, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A. Inorg. Chim. Acta 2007, 360, 1000.
16. Bandini, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A.; Ventrici, C. Chem. Commun. 2007, 616.
17. For previous uses of chiral copper-based weak Lewis acids in enantioselective Henry reactions, see: (a) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. D. J. Am. Chem. Soc. 2003, 725, 12692.
18. (b) Gan, C.; Lai, G.; Zhang, Z.; Wang, Z.; Zhou, M.-M. Tetrahedron: Asymmetry 2006, 17, 725.
19. (c) Maheswaran, H.; Prasanth, K. L.; Krishna, G. G.; Ravikumar, K.; Sridhar, B.; Lakshmi Kantam, M. Chem. Commun. 2006, 4066.
20. (d) Blay, G.; Climent, F.; Fernández, I.; Hernández-Olmos, V.; Pedro, J. R. Tetrahedron: Asymmetry 2006, 17, 2046.
21. (e) Xiong, Y.; Wang, F.; Huang, X.; Wen, Y.; Feng, X. Chem.-Eur. J. 2007, 13, 829.
22. Bandini, M.; Benaglia, M.; Quinto, T.; Tommasi, S.; Umani-Ronchi, A. Adv. Synth. Catal. 2006, 348, 1521.
23. (a) Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325.
24. (b) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.
25. (c) Benaglia, M.; Puglisi, A.: Cozzi, F. Chem. Rev. 2003, 103, 3401.
26. (a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pitillo, M. J. Org. Chem. 2001, 66, 3160.
27. (b) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045.
28. (c) Reger, T. S.; Janda, K. D. J. Am. Chem. Soc. 2000, 122, 6929.
29. (d) Gissibl, A.; Finn, M. G.; Reiser, O. Org. Lett. 2005, 7, 2325.
30. (e) Zhao, D.; Sun, J.; Ding, K. Chem.-Eur. J. 2004, 10, 5952.
31. For the recycle of PEG-supported organometallic chiral catalysts in water, see: (a) Benaglia, M.; Danelli, T.; Pozzi, G. Org. Biomol. Chem. 2003, 1, 454.
32. (b) Benaglia, M.; Cinquini, M.; Cozzi, F.; Celentano, F. Org. Biomol. Chem. 2004, 2, 3401.
33. (c) Li, X.; Wu, X.; Chen, W.; Hancock, F. E.; King, F.; Xiao, J. Org. Lett. 2004, 6, 3321.
34. 2/3 ratio was 10:1.
35. 4CHO) carried out in nitromethane as the solvent led to (S)-4a in 96% conversion and 50% ee.
36. (a) Gao, X.; Kagan, H. B. Chirality 1998, 10, 120.
37. (b) Brouwer, A. J.; Van der Linden, H. J.; Liskamp, R. M. B. J. Org. Chem. 2000, 65, 1750.
38. (c) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773.
39. (d) Satyanarayana, T.; Kagan, H. B. Adv. Synth. Catal. 2005, 347, 737.