The first enantioselective addition of diethylzinc to aldehydes in ionic liquids catalysed by a recyclable ion-tagged diphenylprolinol

Chemistry - A European Journal

Volumn 14, Issue 36, 2008, Pages 11288-11291

  Lombardo, Marco ^a   Chiarucci, Michel ^a   Trombini, Claudio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Asymmetric synthesis; Diethylzinc; Homogeneous catalysis; Ionic liquids; Recycling

Indexed keywords

ALDEHYDES; CATALYSIS; COLLOIDS; ELECTRON TRANSITIONS; GELATION; HYDROFORMYLATION; IONIZATION OF LIQUIDS; IONS; LIQUIDS; ORGANIC COMPOUNDS; REACTION KINETICS; RECYCLING; SILICA; SILICA GEL; SYNTHESIS (CHEMICAL);

AROMATIC ALDEHYDES; ARYL ALDEHYDES; ASYMMETRIC ADDITIONS; ASYMMETRIC SYNTHESIS; CHEMICAL SYNTHESES; CROSS COUPLINGS; DIETHYLZINC; ENANTIOSELECTIVE ADDITIONS; HOMOGENEOUS CATALYSIS;

IONIC LIQUIDS;

EID: 57649217641     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801984     Document Type: Article

References (94)

1. a) H. Weingärtner, Angew. Chem. 2008, 120, 664-682;
2. Angew. Chem. Int. Ed. 2008, 47, 654-670;
3. b) M. Haumann, A. Riisager, Chem. Rev. 2008, 108, 1474-1497;
4. c) M. A. P. Martins, C. P. Frizzo, D. N. Moreira, N. Zanatta, H. G. Bonacorso, Chem. Rev. 2008, 108, 2015-2050;
5. d) T. L. Greaves, C. J. Drummond, Chem. Rev. 2008, 108, 206-237;
6. e) Green Chemical Reactions (Eds.: P. Tundo, V. Esposito), Springer, Heidelberg, 2008;
7. f) Ionic Liquids in Synthesis (Eds.: P. Wasserscheid, T. Welton), Wiley-VCH, Weinheim, 2007;
8. g) F. van Rantwijk, R. A. Sheldon, Chem. Rev. 2007, 107, 2757-2785;
9. h) K. Binnemans, Chem. Rev. 2007, 107, 2592-2614;
10. i) J. Ranke, S. Stolte, R. Stormann, J. Arning, B. Jastorff, Chem. Rev. 2007, 107, 2183-2206;
11. j) V. I. Parvulescu, C. Hardacre, Chem. Rev. 2007, 107, 2615-2665;
12. k) Metal Catalyzed Reactions in Ionic Liquids, (Eds.: P. J. Dyson, T. J. Geldbach), Springer, Heidelberg, 2005;
13. l) Chemistry In Alternative Reaction Media (Eds.: D. Adams, P. J. Dyson, S. Tavener), Wiley, Chichester, 2004;
14. m) Y.-F. Hu, C.-M. Xu, R. D. Rogers, K. R. Seddon, Science 2003, 302, 792-793;
15. n) J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3692;
16. o) T. Welton, Chem. Rev. 1999, 99, 2071-2084.
17. a) P. Migowski, J. Dupont, Chem. Eur. J. 2007, 13, 32-39;
18. b) Z. Fei, T. J. Geldbach, D. Zhao, P. J. Dyson, Chem. Eur. J. 2006, 12, 2122-2130;
19. c) Multiphase Homogeneous Catalysis (Eds.: B. Comils, W. A. Herrmann, I. T. Horváth, W. Leitner, S. Mecking, H. Olivier-Bourbigou, D. Vogt), Wiley-VCH, Weinheim, 2005.
20. D. J. Cole-Hamilton, Science 2003, 299, 1702-1706.
21. For a recent review on ion-tagged catalysts and their use in RTILs, see: R. Šebesta, I. Kmentová, Š. Toma, Green Chem. 2008, 10, 484-496.
22. a) M. Lombardo, F. Pasi, S. Easwar, C Trombini, Adv. Synth. Catal. 2007, 349, 2061-2065;
23. b) M. Lombardo, M. Chiarucci, C. Trombini, submitted.
24. a) H. Clavier, S. P. Nolan, M. Mauduit, Organometallics 2008, 27, 2287-2292;
25. b) G. Liu, J. Zhang, B. Wu, J. Wang, Org. Lett. 2007, 9, 4263-4266;
26. c) Y. S. Vygodskii, A. S. Shaplov, E. I. Lozinskaya, O. A. Filippov, E. S. Shubina, R. Bandari, M. R. Buchmeiser, Macromolecules 2006, 39, 7821-7830;
27. d) A. Stark, M. Ajam, M. Green, H. G. Raubenheimer, A. Ranwell, B. Ondruschka, Adv. Synth. Catal. 2006, 348, 1934-1941;
28. e) D. B. G. Williams, M. Ajam, A. Ranwell, Organometallics 2006, 25, 3088-3090;
29. f) Q. Yao, M. Sheet, J. Organomet. Chem. 2005, 690, 3577-3584;
30. g) H. Clavier, N. Audic, J. C. Guillemin, M. Mauduit, J. Organomet. Chem. 2005, 690, 3585-3599;
31. h) V. Martinez, J. C. Biais, G. Bravie, D. Astruc, Organometallics 2004, 23, 861-874;
32. i) H. Clavier, L. Boulanger, N. Audic, L. Toupet, M. Mauduit, J. C. Guillemin, Chem. Commun. 2004, 1224-1225;
33. j) N. Audic, H. Clavier, M. Mauduit, J.-C. Guillemin, J. Am. Chem. Soc. 2003, 125, 9248-9249;
34. k) K. E. Gutowski, G. A. Broker, H. D. Willauer, J. G. Huddleston, R. P. Swatloski, J. D. Holbrey, R. D. Rogers, J. Am. Chem. Soc. 2003, 125, 6632-6633;
35. l) Q. W. Yao, Y. L. Zhang, Angew. Chem. 2003, 115, 3517-3520;
36. Angew. Chem. Int. Ed. 2003, 42, 3395-3398;
37. m) D. Semeril, H. Oliver-Bourbigou, C. Bruneau, P. H. Dixneuf, Chem. Commun. 2002, 146-147;
38. n) K. G. Mayo, E. H. Nearhoof, J. J. Kiddle, Org. Lett. 2002, 4, 1567-1570;
39. o) S. Csihony, C. Fischmeister, C. Bruneau, I. T. Horvath, P. H. Dixneuf, New J. Chem. 2002, 26, 1667-1670;
40. p) R. C. Buijsman, E. van Vuuren, J. G. Sterrenburg, Org. Lett. 2001, 3, 3785-3787.
41. a) X. Yang, Z. Fei, D. Zhao, W. H. Ang, Y. Li, P. J. Dyson, Inorg. Chem. 2008, 47, 3292-3297;
42. b) Z. Fei, D. Zhao, D. Pieraccini, W. H. Ang, T. J. Geldbach, R. Scopelliti, C. Chiappe, P. J. Dyson, Organometallics 2007, 26, 1588-1598;
43. c) J.-C. Hierso, J. Boudon, M. Picquet, P. Meunier, Eur. J. Org. Chem. 2007, 583-587;
44. d) J.-H. Li, B.-X. Tang, L.-M. Tao, Y.-X. Xie, Y Liang, M.-B Zhang, J. Org. Chem. 2006, 71, 7488-7490;
45. e) L. Durán Pachón, C. J. Elsevier, G. Rothenberg, Adv. Synth. Catal. 2006, 348, 1705-1710;
46. f) K. Bica, P. Gaertner, Org. Lett. 2006, 8, 733-735;
47. g) R. Wang, B. Twamley, J. M. Shreeve, J. Org. Chem. 2006, 71, 426-429;
48. h) C. Chiappe, D. Pieraccini, D. Zhao, Z. Fei, P. J. Dyson, Adv. Synth. Catal. 2006, 348, 68-74;
49. i) J.-C. Xiao, C. Ye, J. M. Shreeve, Org. Lett. 2005, 7, 1963-1965;
50. j) J.-C. Xiao, J. M. Shreeve, J. Org. Chem. 2005, 70, 3072-3078;
51. k) V. Calo, A. Nacci, A. Monopoli, F. Montingelli, J. Org. Chem. 2005, 70, 6040-6044;
52. l) D. Zhao, Z. Fei, T. J. Geldbach, R. Scopelliti, P. J. Dyson, J. Am. Chem. Soc. 2004, 126, 15876-15882;
53. m) F. McLachlan, C. J. Mathews, P. J. Smith, T. Welton, Organometallics 2003, 22, 5350-5357;
54. n) G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895;
55. o) W. Miao, T. H. Chan, Org. Lett. 2003, 5, 5003-5005;
56. p) J. D. Revell, A. Ganesan, Org. Lett. 2002, 4, 3071-3073.
57. a) L. Leclercq, I. Suisse, F. Agbossou-Niedercorn, Chem. Commun. 2008, 311-313;
58. b) K. Hamza, J. Blum, Eur. J. Org. Chem. 2007, 4706-4710;
59. c) S. Paganelli, A. Perosa, M. Selva, Adv. Synth. Catal. 2007, 349, 1858-1862;
60. d) M. Haumann, K. Dentier, J. Joni, A. Riisager, P. Wasserscheid, Adv. Synth. Catal. 2007, 349, 425-431;
61. e) D. B. G. Williams, M. Ajam, A. Ranwell, Organometallics 2007, 26, 4692-4695;
62. f) J. J. Kim, H. Alper, Chem. Commun. 2005, 3059-3061;
63. g) A. Riisager, R. Fehrmann, S. Flicker, R. van Hal, M. Haumann, P. Wasserscheid Angew. Chem. 2005, 117, 826-830;
64. Angew. Chem. Int. Ed. 2005, 44, 815-819;
65. Angew. Chem. Int. Ed. 2005, 44, 815-819;
66. h) R. P. J. Bronger, S. M. Silva, P. C. J. Kamer, P. W. N. M. van Leeuwen, Dalton Trans. 2004, 1590-1596;
67. i) P. B. Webb, M. F. Sellin, T. E. Kunene, S. Williamson, A. M. Z. Slawin, D. J. Cole-Hamilton, J. Am. Chem. Soc. 2003, 125, 15577-15588;
68. j) M. Marchetti, C. Botteghi, S. Paganelli, M. Taddei Adv. Synth. Catal. 2003, 345, 1229-1236;
69. k) C. P. Mehnert, R. A. Cook, N. C. Dispenziere, M. Afeworki, J. Am. Chem. Soc. 2002, 124, 12932-12933;
70. l) C. C. Brasse, U. Englert, A. Salzer, H. Waffenschmidt, P. Wasserscheid, Organometallics 2000, 19, 3818-3823;
71. m) Y. Chauvin, L. Mussmann, H. Olivier, Angew. Chem. 1995, 107, 2941-2943;
72. Angew. Chem. Int. Ed. Engl. 1995, 34, 2698-2700.
73. a) M. C. Law, K.-Y. Wong, T. H. Chan, Chem. Commun. 2006, 2457-2459;
74. b) M. C. Law, K.-Y. Wong, T. H. Chan, Green Chem. 2004, 6, 241-244;
75. c) C. M. Gordon, C. Ritchie, Green Chem. 2002, 4, 124-128;
76. d) G. W. Kabalka, B. Venkataiah, B. C. Das, Green Chem. 2002, 4, 472-473;
77. e) M. C. Law, K.-Y. Wong, T. H. Chan, Green Chem. 2002, 4, 161-164;
78. f) G. W. Kabalka, R. R. Malladi, Chem. Commun. 2000, 2191-2192;
79. g) C. M. Gordon, A. McCluskey, Chem. Commun. 1999, 1431-1432.
80. a) For a recent review on asymmetric catalysis in RTILs, see: S. V. Malhotra, V. Kumar, V. S. Parmar, Curr. Org. Synth. 2007, 4, 370-380;
81. b) J. Lu, S.-J. Ji, T.-P. Loh, Chem. Commun. 2005, 2345-2347;
82. c) J. Lu, S.-J. Ji, Y.-C. Teo, T.-P. Loh, Tetrahedron Lett. 2005, 46, 7435-7437;
83. d) J. N. Rosa, A. G. Santos, C. A. M. Afonso, J. Mol. Catal. A 2004, 214, 161-165;
84. e) C. Baleizão, B. Gigante, H. Garcia, A. Corma, Green Chem. 2002, 4, 212-214.
85. a) K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676-3701;
86. Angew. Chem. Int. Ed. 2000, 39, 3532-3556;
87. b) D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171;
88. Angew. Chem. Int. Ed. Engl. 1995, 54, 1059-1070.
89. a) J.-C. Kizirian, Chem. Rev. 2008, 108, 140-205;
90. L. Pu, H.-B. Yu, Chem. Rev. 2001, 101, 757-824.
91. J. V. B. Kanth, M. Periasamy, Tetrahedron 1993, 49, 5127-5132.
92. T. R. Jensena, C. P. Schallerb, M. A. Hillmyera, W. B. Tolman, J. Organomet. Chem. 2005, 690, 5881-5891.
93. K. Soai, C. Shimada, M. Takeuchi, M. Itabashi, J. Chem. Soc. Chem. Commun. 1994, 567-568.
94. M. Kitamura, H. Oka, S. Suga, R. Noyori, Org. Synth., 2002, 79, 139-142.