Organocatalysis in water at room temperature with in-flask catalyst recycling

Organic Letters

Volumn 14, Issue 1, 2012, Pages 422-425

  Lipshutz, Bruce H ^a   Ghorai, Subir ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NANOMATERIAL; PROLINE; SURFACTANT; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; MICELLE; SOLUBILITY; TEMPERATURE;

CATALYSIS; MICELLES; MOLECULAR STRUCTURE; NANOSTRUCTURES; PROLINE; SOLUBILITY; SURFACE-ACTIVE AGENTS; TEMPERATURE; WATER;

EID: 84855491461     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol203242r     Document Type: Article

References (63)

1. Hajos, Z. G.; Parrish, D. R. DE 2102623, 1971.
2. Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. 1971, 10, 496-497
3. Deer, U.; Sauer, G.; Wiechert, R. DE 2014757, 1971.
4. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621
5. Acc. Chem. Res. 2004, 37, 487-621 (Eds.: Houk, K. N.; List, B.).
6. Tetrahedron 2006, 62, 255-502. (Eds.: Kocovsky, P.; Malkov, A. V.).
7. Chem. Rev. 2007, 107, 5413-5883 (Ed.: List, B.).
8. Moisan, L.; Dalko, P. I. Angew. Chem., Int. Ed. 2001, 40, 3840-3864
9. Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495
10. List, B. Chem. Commun. 2006, 819-824
11. Doyel, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743
12. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569
13. Barbas, C. F. Angew. Chem., Int. Ed. 2008, 47, 42-47
14. Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638-4660
15. Bella, M.; Gasperi, T. Synthesis 2009, 1583-1614
16. Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600-1632
17. Núnez, M. G.; Garcia, P.; Moro, R. F.; Diez, D. Tetrahedron 2010, 66, 2089-2109
18. Johnston, J. N. J. Am. Chem. Soc. 2011, 133, 2330
19. Tietze, L. F.; Brasche, G.; Gerke, K. Domino Reactions in Organic Chemistry; Wiley-VCH: Weinheim, Germany, 2007.
20. Brandau, S.; Maerten, E.; Jorgensen, K. A. J. Am. Chem. Soc. 2006, 128, 14986-14991
21. Hong, B.-C.; Wu, M.-F.; Tseng, H.-C.; Liao, J.-H. Org. Lett. 2006, 8, 2217-2220
22. Enders, D.; Huettl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861-863
23. Carlone, A.; Cabreea, S.; Marigo, M.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1101-1104
24. Hayashi, Y.; Okano, T.; Aratake, S.; Hazelard, D. Angew. Chem., Int. Ed. 2007, 46, 4922-4925
25. Enders, D.; Hüttl, M. R. M.; Runsink, J.; Raabe, G.; Wendt, B. Angew. Chem., Int. Ed. 2007, 46, 467-469
26. Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051-15053
27. Zlotin, S. G.; Kucherenko, A. S.; Beletskaya, I. P. Russ. Chem. Rev. 2009, 78, 737-784
28. Sakthivel, K.; Notz, W.; Bui, T; Barbas, C. F. J. Am. Chem. Soc. 2001, 123, 5260-5267
29. Tang, Z.; Yang, Z. H.; Chen, X. H.; Cun, L. F.; Mi, A. Q.; Jiang, Y. Z.; Gong, L. Z. J. Am. Chem. Soc. 2005, 127, 9285-9289
30. Samanta, S.; Liu, J. Y.; Dodda, R.; Zhao, C. G. Org. Lett. 2005, 7, 5321-5323
31. Guillena, G.; Hita, M. C.; Nájera, C. Tetrahedron: Asymmetry 2006, 17, 1493-1497
32. Gandhi, S.; Singh, V. K. J. Org. Chem. 2008, 73, 9411-9416
33. Hayashi, Y.; Sumiya, T.; Takahashi, J.; Gotoh, H.; Urushima, T.; Shoji, M. Angew. Chem., Int. Ed. 2006, 45, 958-961
34. Raj, M.; Singh, V. K. Chem. Commun. 2009, 6687-6703
35. Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F; Barbas, C. F. J. Am. Chem. Soc. 2006, 128, 734-735
36. Mase, N.; Watanabe, K.; Yoda, H.; Takabe, K.; Tanaka, F; Barbas, C. F. J. Am. Chem. Soc. 2006, 128, 4966-4967
37. For a review, see: Mase, N.; Barbas, C. F. Org. Biomol. Chem. 2010, 8, 4043-4050
38. Mase, N.; Noshiro, N.; Mokuya, A.; Takabe, K. Adv. Synth. Catal. 2009, 351, 2791-2796
39. Hayashi, Y.; Aratake, S.; Okano, T.; Takahashi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2006, 45, 5527-5529
40. Lei, M.; Shi, L.; Li, G.; Chen, S.; Fang, W.; Ge, Z.; Cheng, T.; Li, R. Tetrahedron 2007, 63, 7892-7898
41. Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem., Int. Ed. 2006, 45, 8100-8102
42. Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 8103-8104
43. Huang, J.; Zhang, X.; Armstrong, D. W. Angew. Chem., Int. Ed. 2007, 46, 9073-9077
44. Font, D.; Sayalero, S.; Bastero, A.; Jimeno, C.; Pericàs, M. A. Org. Lett. 2008, 10, 337-340
45. Yan, J.; Wang, L. Synthesis 2008, 2065-2072
46. Wu, Y.; Zhang, Y.; Yu, M.; Zhao, G.; Wang, S. Org. Lett. 2006, 8, 4417-4420
47. Gruttadauria, M.; Giacalone, F.; Noto, R. Chem. Soc. Rev. 2008, 37, 1666-1688 and references therein.
48. Sheldon, R. A.; Arends, I. W. C. E.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
49. Lipshutz, B. H.; Ghorai, S. Org. Lett. 2009, 11, 705-708
50. Lipshutz, B. H.; Ghorai, S. Tetrahedron 2010, 66, 1057-1063
51. Moser, R.; Ghorai, S.; Lipshutz, B. H. Unpublished.
52. Barrett, A. G. M.; Pilipauskas, D. J. Org. Chem. 1991, 56, 2787-2800
53. Borkovec, M. Measuring particle size by light scattering. Handbook of Applied Surface and Colloid Chemistry; John Wiley & Sons Ltd.: Chichester, U.K., 2002; pp 357-370.
54. Hernández, J. G.; Juaristi, E. J. Org. Chem. 2011, 76, 1464-1467
55. Pedrosa, R.; Andrés, J. M.; Manzano, R.; Román, D.; Téllez, S. Org. Biomol. Chem. 2011, 9, 935-940
56. Ricci, A.; Bernardi, L.; Gioia, C.; Vierucci, S.; Robitzer, M.; Quignard, F. Chem. Commun. 2010, 6288-6290
57. Font, D.; Jimeno, C.; Pericàs, M. A. Org. Lett. 2006, 8, 4653-4655
58. Kristensen, T. E.; Vestli, K.; Fredriksen, K. A.; Hansen, F. K.; Hansen, T. Org. Lett. 2009, 11, 2968-2971
59. Lombardo, M.; Easwar, S.; Marco, A. D.; Pasi, F.; Trombini, C. Org. Biomol. Chem. 2008, 6, 4224-4229. See also refs 7b and 8a
60. Hayashi, Y.; Itoh, T.; Aratake, S.; Ishikawa, H. Angew. Chem., Int. Ed. 2008, 47, 2082-2084
61. Hayashi, Y.; Samanta, S.; Itoh, T.; Ishikawa, H. Org. Lett. 2008, 10, 5581-5583
62. Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794-797
63. Zheng, Z.; Perkins, B. L.; Ni, B. J. Am. Chem. Soc. 2010, 132, 50-51