Rationalizing the stereoselectivity of osmium tetroxide asymmetric dihydroxylations with transition state modeling using quantum mechanics- guided molecular mechanics

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 10186-10192

  Norrby, Per Ola ^a   Rasmussen, Torben ^a   Haller, Jan ^b   Strassner, Thomas ^b   Houk, K N ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OSMIUM TETRAOXIDE;

ARTICLE; ENANTIOMER; HYDROLYSIS; MOLECULAR DYNAMICS; QUANTUM MECHANICS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033520791     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992023n     Document Type: Article

References (86)

1. Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
2. (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 227-272.
3. (b) Lohray, B. B. Tetrahedron: Asymmetry 1992, 3, 1317-1349.
4. (c) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis; Beller, M., BoIm, C., Eds.; VCH: Weinheim, 1998; Vol. 2, pp 219-242.
5. (d) Svendsen, J. S.; Markó, I. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Yamamoto, H., Eds.; Springer-Verlag: New York, in press. See also:
6. (e) Jørgensen, K. A. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; VCH: Weinheim, 1998; Vol. 2, pp 157-172.
7. Sharpless, K. B.; Amberg, W.; Beller, M.; Chen, H.; Hartung, J.; Kawanami, Y.; Lübben, D.; Manoury, E.; Ogino, Y.; Shibata, T.; Ukita, T. J. Org. Chem. 1991, 56, 4585-4588.
8. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
9. Kolb, H. C.; Andersson, P. G.; Bennani, Y. L.; Crispino, G. A.; Jeong, K.-Y.; Kwong, H.-L.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 12226-12227.
10. (a) Svendsen, J. S.; Markó, I.; Jacobsen, E. N.; Rao, C. P.; Bott, S.; Sharpless, K. B. J. Org. Chem. 1989, 54, 2263-2264.
11. (b) Pearlstein, R. M.; Blackburn, B. K.; Davis, W. M.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1990, 29, 639-641.
12. Wai, J. S. M.; Markó, I.; Svendsen, J. S.; Finn, M. G.; Jacobsen, E. N.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 1123-1125.
13. (a) Kwong, H.-L.; Sorato, C.; Ogino, Y.; Chen, H.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 2999-3002.
14. (b) Ogino, Y.; Chen, H.; Kwong, H.-L.; Sharpless, K. B. Tetrahedron Lett. 1991, 32, 3965-3968.
15. Criegee, R. Justus Liebigs Ann. Chem. 1936, 522, 75-96.
16. (a) Sharpless, K. B.; Teranishi, A. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120-3128.
17. (b) Hentges, S. G.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 4263-4265.
18. (c) Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 0, 1483-1506.
19. Norrby, P.-O.; Gable, K. P. J. Chem. Soc., Perkin Trans. 2 1996, 171-178.
20. Göbel, T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 1329-1331.
21. Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 319-329.
22. Ujaque, G.; Maseras, F.; Lledós, A. J. Org. Chem. 1997, 62, 7892-7894.
23. Kolb, H. C.; Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 1278-1291.
24. Nelson, D. W.; Sharpless, K. B.; Gypser, A.; Ho, P. T.; Kolb, H. C.; Kondo, T.; Kwong, H.-L.; McGrath, D. V.; Rubin, A. E.; Norrby, P.-O.; Gable, K. P. J. Am. Chem. Soc. 1997, 119, 1840-1858.
25. (a) Jørgensen, K. A.; Hoffmann, R. J. Am. Chem. Soc. 1986, 108, 1867-1876.
26. (b) Jørgensen, K. A. Tetrahedron Lett. 1990, 31, 6417-6420.
27. (a) Rappé, A. K.; Goddard, W. A., III. J. Am. Chem. Soc. 1982, 104, 3287-3294.
28. (b) Norrby, P.-O.; Kolb, H. C.; Sharpless, K. B. Organometallics 1994, 13, 344-347.
29. (c) Veldkamp, A.; Frenking, G. J. Am. Chem. Soc. 1994, 116, 4937-4946.
30. (d) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc., 1996, 118, 35-42.
31. (a) Pidun, U.; Boehme, C.; Frenking, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2817-2820.
32. (b) Dapprich, S.; Ujaque, G.; Maseras, F.; Lledós, A.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1996, 118, 11660-11661.
33. (c) Torrent, M.; Deng, L.; Duran, M.; Sola, M.; Ziegler, T. Organometallics 1997, 16, 13-19.
34. DelMonte, A. J.; Haller, J.; Houk, K. N.; Sharpless, K. B.; Singleton, D. A.; Strassner, T.; Thomas, A. A. J. Am. Chem. Soc. 1997, 119, 9907-9908.
35. Corey, E. J.; Noe, M. C.; Grogan, M. J. Tetrahedron Lett. 1996, 37, 4899-4902.
36. Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 8031-8034.
37. Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7047-7048.
38. Norrby, P.-O.; KoIb, H. C.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 8470-8478.
39. Becker, H.; Ho, P. T.; Kolb, H. C.; Loren, S.; Norrby, P.-O.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 7315-7318.
40. (a) Corey, E. J.; Noe, M. C.; Sarshar, S. Tetrahedron Lett. 1994, 35, 2861-2864.
41. (b) Corey, E. J.; Noe, M. C.; Grogan, M. J. Tetrahedron Lett. 1994, 35, 6427-6430.
42. Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053, and references therein.
43. Ujaque, G.; Maseras, F.; Lledós, A. J. Am. Chem. Soc. 1999, 121, 1317-1323.
44. Eksterowicz, J. E.; Houk, K. N. Chem. Rev. 1993, 93, 2439-2461.
45. Wu, Y.-D.; Wang, Y.; Houk, K. N. J. Org. Chem. 1992, 57, 1362-1369.
46. Gundertofte, K.; Liljefors, T.; Norrby, P.-O.; Pettersson, I. J. Comput. Chem. 1996, 17, 429-449.
47. (a) Houk, K. N.; Rondan, N. G.; Wu, Y.-D.; Metz, J. T.; Paddon-Row, M. N. Tetrahedron 1984, 12, 2257-2274.
48. (b) Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108-1117.
49. Brown, F. K.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 1971-1978.
50. Thomas, B. E., IV.; Loncharich, R. J.; Houk, K. N. J. Org. Chem. 1992, 57, 1354-1362.
51. (a) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974.
52. (b) Broeker, J. L.; Houk, K. N. J. Org. Chem. 1991, 56, 3651-3655.
53. (a) Wu, Y.-D.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 908-910.
54. (b) Wu, Y.-D.; Houk, K. N.; Trost, B. M. J. Am. Chem. Soc. 1987, 109, 5560-5561.
55. (c) Mukherjee, D.; Wu, Y.-D.; Fronczek, F. R.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 3328-3330.
56. (d) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664.
57. Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613-2636.
58. Norrby, P.-O. In Transition State Modeling for Catalysis: Truhlar, D. G., Morokuma, K., Eds.; ACS Symposium Series No. 721, 1999; Chapter 13, pp 163-172.
59. (a) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284-8294.
60. (b) Norrby, P.-O.; Brandt, P.; Rein, T. J. Org. Chem, 1999, 64, 5845-5852.
61. 3) (internally type 26) in the structure file before calculations can be run.
62. In calculated ammine complexes, the N-H bonds are eclipsed with the Os=O bonds. Using a tertiary amine, the C-N bonds are now staggered with the Os=O bonds, in accordance with known structures (ref 6).
63. Dasgupta, S.; Goddard, W. A., III J. Chem. Phys. 1989, 90, 7207-7215.
64. Maple, J. R.; Hwang, M.-J.; Stockfisch, T. P.; Dinur, U.; Waldman, M.; Ewig, C. S.; Hagler, A. T. J. Comput. Chem. 1994, 15, 162-182.
65. Halgren, T. A. J. Comput. Chem. 1996, 17, 490-519.
66. Norrby, P.-O.; Liljefors, T. J. Comput. Chem. 1998, 19, 1146-1166.
67. Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551-8566.
68. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361-373.
69. Brandt, P.; Norrby, T.; Åkermark, B.; Norrby, P.-O. Inorg. Chem. 1998, 37, 4120-4127.
70. We have ignored possible differences in solvation energy and vibrational contributions, as these can be expected to cancel in a comparison of diastereomeric structures with low polarity.
71. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheesemen, J. R.; Keith, T. A.; Petersson, J. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. Gaussian 94; Gaussian Inc.: Pittsburgh, PA, 1995.
72. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
73. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, 37, 785-789.
74. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
75. MacroModel, V6.0; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467. Note! A bug in MacroModel will give serious errors if conformational searches are performed using force fields with geometry-dependent parameters (like the current force field). It is necessary to divide the searches into groups where all structures have the same parameter values, and to ensure (by constraints) that no crossover takes place. Starting from V6.5, correct behavior can be obtained using the "DEBG 57" command.
76. MacroModel, V6.0; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467. Note! A bug in MacroModel will give serious errors if conformational searches are performed using force fields with geometry-dependent parameters (like the current force field). It is necessary to divide the searches into groups where all structures have the same parameter values, and to ensure (by constraints) that no crossover takes place. Starting from V6.5, correct behavior can be obtained using the "DEBG 57" command.
77. MM3* is based on the MM3(91) force field (ref 46). The major differences are: A substructure-matching scheme in lieu of the π-system calculation; use of atomic charges only, no dipoles; nondirectional hydrogen bonding adapted from the Amber* force field.
78. Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110-1117.
79. Kolossvary, J.; Guida, W. C. J. Am. Chem. Soc. 1996, 118, 5011-5019.
80. A MacroModel force field file can be downloaded in a directly usuable format from http://compchem.dfh.dk/PeO/.
81. For examples of exceptions, see: (a) Jensen, F. J. Comput. Chem. 1994, 15, 1199-1216.
82. (b) Åqvist, J.; Warehel, A. Chem. Rev. 1993, 93, 2523-2544.
83. As a personal experience, introduction of force field methods into selectivity predictions has previously been limited by the long development time; by the time the model was finished, the synthetic project could easily have moved into another phase or been abandoned altogether.
84. Note that when comparing enantioselectivities, the accuracy is not the same in the entire range. For example, assuming that the calculations are accurate to within ∼2 kJ/mol (see Supporting Information and ref 31), a predicted ee of 99.0% should fall within the range 97.7-99.5%, whereas the same accuracy in energy for a predicted value of 75% would correspond to the range 51-88%.
85. The orientation shown in Figure 5 is strongly favored for all ligands in the current study.
86. Sharpless, K. B.; Wang, L., unpublished data. Private communication from K. Barry Sharpless and Bruce Bender.