Theoretical studies of stereoselectivities of intramolecular aldol cyclizations catalyzed by amino acids

Journal of the American Chemical Society

Volumn 127, Issue 32, 2005, Pages 11294-11302

  Clemente, Fernando R ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYST SELECTIVITY; CATALYSTS; CHEMICAL BONDS; KETONES; PROBABILITY DENSITY FUNCTION; SUBSTITUTION REACTIONS;

ALDOLS; DENSITY FUNCTION THEORY; INTRAMOLECULES; STEREOSELECTIVITIES;

ALDEHYDES;

AMINO ACID; KETONE; METHYL GROUP; PROLINE;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

ALDEHYDES; AMINO ACIDS; CATALYSIS; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 23844543306     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0507620     Document Type: Article

References (60)

1. (a) Hajos, Z. G.; Parrish, D. R. German Patent DE 2102623, Jul 29, 1971.
2. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621.
3. (c) Eder, U.; Sauer, G.; Wiechert, R. German Patent DE 2014757, Oct 7, 1971.
4. (d) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497.
5. (e) Ruppert, J.; Eder, U.; Wiechert, R. Chem. Ber. 1973, 106, 3636-3644.
6. (a) Danishefsky, S.; Cain, P. J. Am. Chem. Soc. 1976, 98, 4975-4983.
7. (b) Cohen, N. Acc. Chem. Res. 1976, 9, 412-417.
8. (c) Smith, A. B., III; Kingery-Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449.
9. (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126-8127.
10. (e) Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38. 2081-2084.
11. (f) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; DiGrandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859.
12. (a) Buchschacher, P.; Cassai, J.-M.; Fürst, A.; Meier, W. Helv. Chim. Acta 1977, 60, 2747-2755.
13. (b) Takano, S.; Kasahara, C.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1981, 635-637.
14. (c) Tamai, Y.; Mizutani, Y.; Hagiwara, H.; Uda, H.; Harada, N. J. Chem. Res. (M) 1985, 1746-1787.
15. (d) Rajagopal, D.; Narayanan, R.; Swaminathan, S. Tetrahedron Lett. 2001, 42, 4887-4890.
16. Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17.
17. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951-6954.
18. Rajagopal, D.; Rajagopalan, K.; Swaminathan, S. Tetrahedron: Asymmetry 1996, 7, 2189-2190.
19. (a) Wang, K. C.; Kan, W.-M.; Gau, C.-S. J. Taiwan Pharm. Assoc. 1986, 38, 6-9.
20. (b) Wang, K. C.; Huang, J.-D. J. Taiwan Pharm. Assoc. 1978, 30, 160-169.
21. Martens, J.; Lüben, S. Arch. Pharm. (Weinheim) 1991, 324, 59-60.
22. Medarde, M.; Caballero, E.; Melero, C. P.; Tomé, F.; San Feliciano, A. Tetrahedron: Asymmetry 1997, 8, 2075-2077.
23. Banerjee, D. K.; Kasturi, T. R.; Sarkar, A. Proc. Indian Acad. Sci. (Chem. Sci.) 1983, 92, 181-187.
24. (a) Shimizu, I.; Naito, Y.; Tsuji, J. Tetrahedron Lett. 1980, 21, 487-490.
25. (b) Takahashi, S.; Oritani, T.; Yamashita, K. Agric. Biol. Chem. 1987, 51, 2291-2293.
26. (c) Hagiwara, H.; Uda, H. J. Org. Chem. 1988, 53, 2308-2311.
27. (d) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431.
28. (e) Przezdziecka, A.; Stepanenko, W.; Wicha, J. Tetrahedron: Asymmetry 1999, 10, 1589-1598.
29. Mander, L. N.; Turner, J. V. Tetrahedron Lett. 1981, 22, 3683-3686.
30. Gutzwiller, J.; Buchschacher, P.; Fürst, A. Synthesis 1977, 167-168.
31. Coisne, J.-M.; Pecher, J. Bull. Soc. Chim. Belg. 1981, 90, 481-484.
32. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267.
33. (a) Jung, M. E. Tetrahedron 1976, 32, 3-31.
34. (b) Corrected configuration of the carbinolamine intermediate as suggested in ref 16a.
35. Spencer, T. A.; Neel, H. S.; Flechtner, T. W.; Zayle, R. A. Tetrahedron Lett. 1965, 43, 3889-3897.
36. Molines, H.; Wakselman, C. Tetrahedron 1976, 32, 2099-2103.
37. (a) Agami, C.; Meynier, F.; Puchot, C.; Guilhem, J.; Pascard, C. Tetrahedron 1984, 40, 1031-1038.
38. (b) Agami, C. Bull. Soc. Chim. Fr. 1988, 3, 499-507.
39. (a) Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442.
40. (b) Agami, C.; Puchot, C. J. Mol. Catal. 1986, 38, 341-343.
41. Brown, K. L.; Damm, L.; Dunitz, J. D.; Eschenmoser, A.; Hobi, R.; Kratky, C. Helv. Chim. Acta 1978, 61, 3108-3135.
42. List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396.
43. List, B.; Hoang, L.; Martin, H. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5839-5842.
44. Clemente, F. R.; Houk, K. N. Angew. Chem., Int. Ed. 2004, 43, 5766-5768.
45. (a) Takano, Y.; Houk, K. N. J. Chem. Theory Comput. 2005, 1, 70-77.
46. (b) Mennucci, B.; Cammi, R.; Tomasi, J. J. Chem. Phys. 1999, 110, 6858-6870.
47. (c) Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
48. Frisch, M. J.; et al. Gaussian 98. Revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
49. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
50. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
51. (a) Allemann, C.; Gordillo, R.; Clemente, F. R.; Cheong, P. H.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558-569.
52. (b) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273-11283.
53. (c) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 12911-12912.
54. (d) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479.
55. (e) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251.
56. ὼ parameters are commonly used to describe out-of-plane deformations of enamines or amides; see ref 21.
57. Cannizzaro, C. E.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 7163-7169.
58. (a) Agami, C.; Sevestre, H. J. Chem. Soc., Chem. Commun. 1984, 21, 1385.
59. (b) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358-360.
60. Del Bene, J. E.; Person, W. B.; Szczepaniak. K. J. Phys. Chem. 1995, 99, 10705-10707.