Highly Enantioselective Cross-Aldol Reactions of Acetaldehyde Mediated by a Dual Catalytic System Operating under Site Isolation

Chemistry - A European Journal

Volumn 20, Issue 41, 2014, Pages 13089-13093

  Fan, Xinyuan ^a   Rodríguez Escrich, Carles ^a   Wang, Shoulei ^a   Sayalero, Sonia ^a   Pericàs, Miquel A ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

acetaldehyde; cross aldol; recycling; site isolation; wolf and lamb

Indexed keywords

ACETALDEHYDE; CATALYSTS; CHEMICAL REACTIONS; ENANTIOSELECTIVITY; RECYCLING;

CATALYTIC SYSTEM; CROSS-ALDOL; CROSS-ALDOL REACTION; ENANTIOSELECTIVE; SITE ISOLATION; TRIFLUOROMETHYL; TWO-STEP SYNTHESIS; WOLF AND LAMB;

KETONES;

EID: 84941072850     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404215     Document Type: Article

References (72)

1. R. Mahrwald, Chem. Rev. 1999, 99, 1095-1120;
2. T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430;
3. Angew. Chem. Int. Ed. 2000, 39, 1352-1375;
4. C. Palomo, M. Oiarbide, J. M. Garcia, Chem. Soc. Rev. 2004, 33, 65-75;
5. B. M. Trost, C. S. Brindle, Chem. Soc. Rev. 2010, 39, 1600-1632.
6. C. Allemann, R. Gordillo, F. R. Clemente, P. H.-Y. Cheong, K. N. Houk, Acc. Chem. Res. 2004, 37, 558-569;
7. W. Notz, F. Tanaka, C. F. Barbas, Acc. Chem. Res. 2004, 37, 580-591;
8. S. Saito, H. Yamamoto, Acc. Chem. Res. 2004, 37, 570-579;
9. A. P. Brogan, T. J. Dickerson, K. D. Janda, Angew. Chem. 2006, 118, 8278-8280;
10. Angew. Chem. Int. Ed. 2006, 45, 8100-8102;
11. D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590-1601;
12. Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
13. G. Guillena, C. Nájera, D. J. Ramõn, Tetrahedron: Asymmetry 2007, 18, 2249-2293;
14. V. Bisai, A. Bisai, V. K. Singh, Tetrahedron 2012, 68, 4541-4580;
15. M. M. Heravi, S. Asadi, Tetrahedron: Asymmetry 2012, 23, 1431-1465;
16. G. Guillena, in Modern Methods in Stereoselective Aldol Reactions, Wiley-VCH, 2013, pp. 155-268;
17. J. Mlynarski, S. Bas, Chem. Soc. Rev. 2014, 43, 577-587.
18. B. List, R. A. Lerner, C. F. Barbas, J. Am. Chem. Soc. 2000, 122, 2395-2396.
19. B. Alcaide, P. Almendros, Angew. Chem. 2008, 120, 4710-4712;
20. Angew. Chem. Int. Ed. 2008, 47, 4632-4634.
21. Y. Hayashi, T. Itoh, S. Aratake, H. Ishikawa, Angew. Chem. 2008, 120, 2112-2114;
22. Angew. Chem. Int. Ed. 2008, 47, 2082-2084;
23. Y. Hayashi, S. Samanta, T. Itoh, H. Ishikawa, Org. Lett. 2008, 10, 5581-5583.
24. S. Hu, L. Zhang, J. Li, S. Luo, J.-P. Cheng, Eur. J. Org. Chem. 2011, 3347-3352.
25. Y. Qiao, Q. Chen, S. Lin, B. Ni, A. D. Headley, J. Org. Chem. 2013, 78, 2693-2697.
26. M. Kumar, B. A. Shah, S. C. Taneja, Adv. Synth. Catal. 2011, 353, 1207-1212.
27. E. Alza, M. A. Pericàs, Adv. Synth. Catal. 2009, 351, 3051-3056;
28. E. Alza, S. Sayalero, P. Kasaplar, D. Almaşi, M. A. Pericàs, Chem. Eur. J. 2011, 17, 11585-11595;
29. E. Alza, S. Sayalero, X. C. Cambeiro, R. Martin-Rapun, P. O. Miranda, M. A. Pericàs, Synlett 2011, 464-468;
30. P. Riente, C. Mendoza, M. A. Pericàs, J. Mater. Chem. 2011, 21, 7350-7355;
31. X. Fan, S. Sayalero, M. A. Pericàs, Adv. Synth. Catal. 2012, 354, 2971-2976.
32. B. J. Cohen, M. A. Kraus, A. Patchornik, J. Am. Chem. Soc. 1981, 103, 7620-7629;
33. T. H. Maugh, Science 1982, 217, 719-720.
34. X. Fan, C. Rodríguez-Escrich, S. Sayalero, M. A. Pericàs, Chem. Eur. J. 2013, 19, 10814-10817.
35. S. Hecht, J. M. J. Fréchet, Angew. Chem. 2001, 113, 76-94;
36. Angew. Chem. Int. Ed. 2001, 40, 74-91;
37. B. Voit, Angew. Chem. 2006, 118, 4344-4346;
38. Angew. Chem. Int. Ed. 2006, 45, 4238-4240;
39. K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2005, 127, 9674-9675;
40. B. Helms, S. J. Guillaudeu, Y. Xie, M. McMurdo, C. J. Hawker, J. M. J. Fréchet, Angew. Chem. 2005, 117, 6542-6545;
41. Angew. Chem. Int. Ed. 2005, 44, 6384-6387;
42. M. B. Runge, M. T. Mwangi, A. L. Miller, M. Perring, N. B. Bowden, Angew. Chem. 2008, 120, 949-953;
43. Angew. Chem. Int. Ed. 2008, 47, 935-939;
44. Y. Chi, S. T. Scroggins, J. M. J. Fréchet, J. Am. Chem. Soc. 2008, 130, 6322-6323.
45. N. Zotova, A. Franzke, A. Armstrong, D. G. Blackmond, J. Am. Chem. Soc. 2007, 129, 15100-15101;
46. A. K. Sharma, R. B. Sunoj, Angew. Chem. 2010, 122, 6517-6521;
47. Angew. Chem. Int. Ed. 2010, 49, 6373-6377;
48. J. Ribas-Arino, M. A. Carvajal, A. Chaumont, M. Masia, Chem. Eur. J. 2012, 18, 15868-15874;
49. S. Paladhi, J. Das, P. K. Mishra, J. Dash, Adv. Synth. Catal. 2013, 355, 274-280;
50. Z.-B. Xie, N. Wang, L.-H. Zhou, F. Wan, T. He, Z.-G. Le, X.-Q. Yu, ChemCatChem 2013, 5, 1935-1940.
51. K. A. De Castro, J. Ko, D. Park, S. Park, H. Rhee, Org. Process Res. Dev. 2007, 11, 918-921.
52. M. Sasikumar, M. D. Nikalje, Synth. Commun. 2012, 42, 3061-3067.
53. G. Sabitha, P. Padmaja, J. S. Yadav, Helv. Chim. Acta 2008, 91, 2235-2239.
54. C.-F. Xu, C.-Y. Yuan, Chin. J. Chem. 2004, 22, 775-778.
55. V. Ratovelomanana-Vidal, C. Girard, R. Touati, J. P. Tranchier, B. B. Hassine, J. P. Genêt, Adv. Synth. Catal. 2003, 345, 261-274;
56. H. Kakei, T. Nemoto, T. Ohshima, M. Shibasaki, Angew. Chem. 2004, 116, 321-324;
57. Angew. Chem. Int. Ed. 2004, 43, 317-320;
58. Â. de Fátima, A. A. M. Lapis, R. A. Pilli, J. Braz. Chem. Soc. 2005, 16, 495-499;
59. D. Liu, W. Gao, C. Wang, X. Zhang, Angew. Chem. 2005, 117, 1715-1717;
60. Angew. Chem. Int. Ed. 2005, 44, 1687-1689;
61. R. K. Rej, T. Das, S. Hazra, S. Nanda, Tetrahedron: Asymmetry 2013, 24, 913-918.
62. Y. Gao, K. B. Sharpless, J. Org. Chem. 1988, 53, 4081-4084.
63. P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840-3864;
64. Angew. Chem. Int. Ed. 2001, 40, 3726-3748;
65. K. N. Houk, B. List, Acc. Chem. Res. 2004, 37, 487-487;
66. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286;
67. Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
68. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178-2189;
69. D. W. C. MacMillan, Nature 2008, 455, 304-308.
70. C. L. Duc, C. Charlon, C. A. Delord, J. Cros, B. Monsarrat, J. Labelled Compd. Radiopharm. 1978, 15, 693-696;
71. M. Fischler, J. C. Levron, H. Trang, J. F. Vaxelaire, B. Flaisler, G. Vourch, Br. J. Anaesth. 1985, 57, 872-876;
72. M. Fischler, J. C. Levron, H. Trang, D. Brodaty, C. Dubois, D. Guilmet, G. Vourch, Br. J. Anaesth. 1985, 57, 877-882.