Mechanism of metal chloride-promoted mukaiyama aldol reactions

Journal of Organic Chemistry

Volumn 72, Issue 4, 2007, Pages 1425-1430

  Chiong, Teck Wong ^a   Ming, Wah Wong ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIER; ENERGY PATHWAY; MUKAIYAMA ALDOL REACTIONS;

ADDITION REACTIONS; CARBON; CATALYSIS; ETHERS; FORMALDEHYDE; SILANES;

CHLORIDE MINERALS;

ALUMINUM CHLORIDE; BORON DERIVATIVE; CHLORIDE; FORMALDEHYDE; GALLIUM CHLORIDE; LEWIS ACID; METAL DERIVATIVE; TITANIUM CHLORIDE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CALCULATION; CHEMICAL BOND; CYCLOADDITION; ENERGY; MUKAIYAMA REACTION; ORGANIC CHEMISTRY;

EID: 33847071218     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062218v     Document Type: Article

References (78)

1. (a) Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
2. (b) Mukaiyama, T.; Izawa, T.; Saigo, K. Chem. Lett. 1974, 323,
3. (c) Mukaiyama, T.; Narasaka, K.; Banno, K. Chem. Lett. 1973, 1011.
4. (d) Mukaiyama, T. Angew. Chem., Int. Ed. 1979, 16, 817.
5. (a) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: New York, 2004.
6. (b) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65.
7. (c) Carreira, E. M. In Comprehensive Asymmetric Catalyst; Jacobsen, R. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Germany, 1999; Vol. 3.
8. (d) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Eur. J. 1998, 4, 36.
9. (e) Groger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 2002, 8, 1137.
10. (f) Chan, T.-H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2.
11. (g) Imashiro, R.; Kuroda, T. J. Org. Chem. 2003, 68, 974.
12. (h) Flowers R. A., II; Xu, X.; Timmons, C.; Li, G. Eur. J. Org. Chem. 2004, 2988.
13. (i) Ooi, T.; Maruoka K. Acc. Chem. Res. 2004, 37, 526.
14. (j) Zhuang, W.; Poulsen, T. B.; Jorgensen, K. A. Org. Biomol. Chem. 2005, 3, 3284.
15. (a) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 112, 9672.
16. (b) Myers, A. G.; Kephart, S. E.; Chen, H. J. Am. Chem. Soc. 1992, 114, 7922.
17. (c) Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. J. Am. Chem. Soc. 1994, 116, 7026.
18. (d) Denmark, S. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 5136.
19. (e) Denmark, S. E.; Griedel, B. D.; Coe, D. M. J. Org. Chem. 1993, 58, 988.
20. (f) Denmark, S. E.; Winter, S. B. D.; Su X.; Wong, K. T. J. Am. Chem. Soc. 1996, 118, 7404.
21. (g) Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585.
22. (h) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
23. Wong, C. T.; Wong, M. W. J. Org. Chem. 2005, 70, 124.
24. Cain, M. J.; Cawley, A.; Sum, V.; Brown, D.; Thornton-Pett, M.; Kee, T. P. Inorg. Chim. Acta 2003, 345, 154.
25. (a) Phukan, P. Synth. Commun. 2004, 34, 1065.
26. (b) Chung, W. J.; Ngo, S. C.; Higashiya, S.; Welch, J. T. Tetrahedron Lett. 2004, 45, 5403.
27. (c) Yang, B.; Chen, X.; Deng, G.; Zhang, Y.; Fan, Q. Tetrahedron Lett. 2003, 44, 3535.
28. (d) Morohashi, N.; Hattori, T.; Yokomakura, K.; Kabuto, C.; Miyano, S. Tetrahedron Lett. 2002, 43, 7769.
29. (e) Zimmer, R.; Peritz, A.; Czerwonka, R.; Schefzig, L.; Reissig, H. Eur. J. Org. Chem. 2002, 3419.
30. (f) Li, H.; Tian, H.; Chen, Y.; Wang, D.; Li, C. Chem. Commun. 2002, 2994.
31. (a) Chancharunee, S.; Perlmutter, P.; Statton, M. Tetrahedron Lett. 2003, 44, 5683.
32. (b) Ishihara, K.; Kondo, S.; Yamamoto, H. Synlett 1999, 8, 1283.
33. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039.
34. Munoz-Muniz, O.; Quintanar-Audelo, M.; Juaristi, E. J. Org. Chem. 2003, 68, 1622.
35. Takasu, K.; Ueno, M.; Inanaga, K.; Ihara, M. J. Org. Chem. 2004, 69, 517.
36. (a) Oisaki, K.; Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5644.
37. (b) Wadamoto, M.; Ozasa, N.; Yanagisawa, A.; Yamamoto, H. J. Org. Chem. 2003, 68, 5593.
38. (c) Ishii, A.; Kojima, J.; Mikami, K. Org. Lett. 1999, 12, 2013.
39. (d) Lin, S.; Bondar, G. V.; Levy, C. J.; Collins, S. J. Org. Chem. 1998, 63, 1885.
40. (e) Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707.
41. Ellis, W. W.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1998, 193.
42. Cozzi, P. G.; Floriani, C. Organometallics 1994, 13, 2131.
43. (a) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564.
44. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
45. (c) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323.
46. Denmark, S. E.; Chen, C. Tetrahedron Lett. 1994, 35, 4327.
47. Gung, B. W.; Zhu, Z.; Fouch, R. A. J. Org. Chem. 1995, 60, 2860.
48. (a) Ohkouchi, M.; Masui, D.; Yamaguchi, M.; Yamagishi, T. J. Mol. Catal. A 2001, 170, 1.
49. (b) Ohkouchi, M.; Yamaguchi, M.; Yamagishi, T. Enantiomer 2000, 5, 71.
50. (a) Reetz, M. T.; Raguse, B.; Marth, C. F.; Huegel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron 1992, 48, 5731.
51. (b) Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754.
52. (a) Hamza, A.; Schubert, G.; Soos, T.; Papai, I. J. Am. Chem. Soc. 2006, 128, 13151.
53. (b) Zhang, X.; Houk, K. N. J. Org. Chem. 2005, 70, 9712.
54. (c) Clemente, R.; Houk, K. N. Angew. Chem., Int. Ed. 2004, 43, 5766.
55. (d) Rankin, K. N.; Gauld, J. W.; Boyd, R. J. J. Phys. Chem. A 2002, 106, 5155.
56. Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322.
57. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
58. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
59. (a) Kurita, N.; Tanaka, S.; Itoh, S. J. Phys. Chem. A 2000, 104, 8114.
60. (b) Tsuzuki, S.; Luthi, H. P. J. Chem. Phys. 2001, 114, 3949.
61. (c) Ujaque, G.; Lee, P. S.; Houk, K. N.; Hentemann, M. F.; Danishefsky, S. Chem. J. Eur. 2002, 8, 3423.
62. (d) Kurita, N.; Sekin, H. Int. J. Quantum Chem. 2003, 91, 355.
63. (e) Ye, X.; Li, Z.-H.; Wang, W.; Fan, K.; Xu, W.; Hua, Z. Chem. Phys. Lett. 2004, 397, 56.
64. Wong, M. W. Chem. Phys. Lett. 1996, 256, 391.
65. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
66. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold F. NBO Version 3.1.
67. Bader, R. F. W. Atoms in Molecules - A Quantum Theory; Oxford Science Publications: Oxford, UK, 1990.
68. (a) Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707.
69. (b) Aggarwal, V. K.; Masters, S. J.; Adams, H.; Spey, S. E.; Brown, G. R.; Foubister, A. J. J. Chem. Soc., Perkin Trans. 1 1995, 155.
70. (c) Zhao, C.; Bass, J.; Morken, J. P. Org. Lett. 2001, 3, 2839.
71. (d) Grimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894.
72. Dahl, T. Acts Chem. Scand. 1994, 48, 95.
73. (a) Ran, J.; Wong, M. W. J. Phys. Chem. A 2006, 110, 9702.
74. (b) Novoa, J. J.; Mota, F. Chem. Phys. Lett. 2000, 318, 45.
75. (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650.
76. (b). Wong, M. W. J. Org. Chem. 2005, 70, 5487.
77. Mukaiyama, T. Pure Appl. Chem. 1983, 11, 1749.
78. Arisawa, M.; Akamatsu, K.; Yamaguchi, M. Org. Lett. 2001, 3, 789.