Modeling the stereoselectivity of the β-amino alcohol-promoted addition of dialkylzinc to aldehydes

Journal of the American Chemical Society

Volumn 125, Issue 17, 2003, Pages 5130-5138

  Rasmussen, Torben ^a,c   Norrby, Per Ola ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; REACTION KINETICS;

ENANTIOSELECTIVITY; LIGANDS;

ALCOHOLS;

ALDEHYDE; AMINOALCOHOL; BETA AMINOALCOHOL; CARBON; CARBONYL DERIVATIVE; ORGANIC COMPOUND; REAGENT; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 0037473518     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0292952     Document Type: Article

References (91)

1. (a) Sato, T.; Soai, K.; Suzuki, K.; Mukaiyama, T. Chem. Lett. 1978, 601-604.
2. (b) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455-1460.
3. (c) Oguni, N.; Omi, T.; Yamamoto, Y.; Nakamura, A. Chem. Lett. 1983, 841-842.
4. (d) Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
5. (e) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072.
6. (f) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140-4142.
7. (g) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690-1691.
8. (h) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111-7115.
9. (i) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 467-468.
10. (j) Smaardijk, A. A.; Wynberg, H. J. Org. Chem. 1987, 52, 135-137.
11. (k) Chaloner, P. A.; Perera, S. A. R. Tetrahedron Lett. 1987, 28, 3013-3014.
12. (l) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877-7878.
13. (m) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
14. (n) Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784-786.
15. (a) Evans, D. A. Science 1988, 240, 420-426.
16. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
17. (c) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
18. (d) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824.
19. (a) Tanner, D.; Kornø, H. T.; Guijarro, D.; Andersson, P. G. Tetrahedron 1998, 54, 14213-14232.
20. (b) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492.
21. (c) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078-7082.
22. (d) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530-2535.
23. (e) Shi, M.; Satoh, Y.; Masaki, Y. J. Chem. Soc., Perkin Trans. 1 1998, 2547-2552.
24. (f) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K. Tetrahedron: Assymetry 1999, 10, 133-138.
25. (g) Wassmann, S.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1999, 10, 4437-4445.
26. (h) Sibi, M. P.; Chen, J.-X.; Cook, G. R. Tetrahedron Lett. 1999, 40, 3301-3304.
27. (i) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 10, 1571-1572.
28. (j) Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353-2365.
29. (k) Paleo, M. R.; Cabeza, I.; Sardina, F. J. J. Org. Chem. 2000, 65, 2108-2113.
30. (l) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. Synthesis 2000, 1, 165-176.
31. (m) Kawanami, Y.; Mitsuie, T.; Miki, M.; Sakamoto, T.; Nishitani, K. Tetrahedron 2000, 56, 175-178.
32. (n) Dai, W.-M.; Zhu, H.-J.; Hao, X.-J. Tetrahedron: Asymmetry 2000, 11, 2315-2337.
33. (o) Ooi, T.; Saito, A.; Maruoka, K. Chem. Lett. 2001, 1108-1109.
34. (p) Hu, Q.-S.; Sun, C.; Monaghan, C. E. Tetrahedron Lett. 2001, 42, 7725-7728.
35. (q) Ohga, T.; Umeda, S.; Kawanami, Y. Tetrahedron 2001, 57, 4825-4829.
36. (r) Steiner, D.; Sethofer, S. G.; Goralski, C. T.; Singaram, B. Tetrahedron: Asymmetry 2002, 13, 1477-1483.
37. (s) Xu, Q.; Zhu, G.; Pan, X.; Chan, A. S. C. Chirality 2002, 14, 716-723.
38. (t) Sato, I.; Kodaka, R.; Hosoi, K.; Soai, K. Tetrahedron: Asymmetry 2002, 13, 805-808.
39. (a) Dosa, P. I.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444-445.
40. (b) Huang, W.-S.; Pu, L. J. Org. Chem. 1999, 64, 4222-4223.
41. (c) Bolm, C.; Muñiz, K. Chem. Commun. 1999, 1295-1296.
42. (d) Bolm, C.; Hildebrand, J. P.; Muñiz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284-3308.
43. (e) Bolm, C.; Hermanns, N.; Kesselgruber, M.; Hildebrand, J. P. J. Organomet. Chem. 2001, 624, 157-161.
44. (f) Zhao, G.; Li, X.-G.; Wang, X.-R. Tetrahedron: Asymmetry 2001, 12, 399-403.
45. (g) Ko, D.-H.; Kim, K. H.; Ha, D.-C. Org. Lett. 2002, 4, 3759-3762.
46. (h) Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124, 14850-14851.
47. (a) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327-6335.
48. (b) Yamakawa, M.; Noyori, R. Organometallics 1999, 18, 128-133.
49. (a) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R.; Zhai, Z.-X.; Suga, H. J. Phys. Chem. 1994, 98, 12776-12781.
50. (b) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832-4842.
51. (c) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800-9809.
52. (d) Kitamura, M.; Oka, H.; Noyori, R. Tetrahedron 1999, 55, 3605-3614.
53. We use the terms "catalytic zinc" to designate the zinc atom permanently coordinated to the bidentate ligand, "substrate" for the reacting aldehyde, and "reagent" for the dialkyl zink species that is coordinated to the oxygen of the catalyst for part of the catalytic cycle. The α-position designates the carbon directly connected to the alkoxide oxygen, whereas the β-position is the backbone carbon atom bound directly to the nitrogen.
54. Soai, K.; Shibata, T. Asymmetric Amplification and Autocatalysis. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 699-725.
55. The catalyst dimers need not be inactive for other types of ligands: Blackmond, D. G.; McMillan, C. R.; Ramdeehul, S.; Schorm, A.; Brown, J. M. J. Am. Chem. Soc. 2001, 123, 10103-10104.
56. Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem.-Eur. J. 2002, 8, 5211-5218.
57. Rasmussen, T.; Norrby, P.-O. J. Am. Chem. Soc. 2001, 123, 2464-2465.
58. Note that inv implies that the substrate and reagent coordinate to the face of the catalyst with the highest steric bulk.
59. (a) Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1997, 38, 8773-8776.
60. (b) Goldfuss, B.; Houk, K. N. J. Org. Chem. 1998, 63, 8998-9006.
61. (c) Goldfuss, B.; Steigelmann, M.; Khan, S. I.; Houk, K. N. J. Org. Chem. 2000, 65, 77-82.
62. (d) Goldfuss, B.; Steigelmann, M.; Rominger, F. Eur. J. Org. Chem. 2000, 1785-1792.
63. (e) Vázquez, J.; Pericàs, M. A.; Maseras, F.; Lledós, A. J. Org. Chem. 2000, 65, 7303-7309.
64. (f) Panda, M.; Phuan, P.-W.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 564-571.
65. Norrby, P.-O. J. Mol. Struct. (THEOCHEM) 2000, 506, 9-16.
66. Jensen, F.; Norrby, P.-O. Theor. Chem. Acc. 2003, 109, 1-7.
67. Eksterowicz, J. E.; Houk, K. N. Chem. Rev. 1993, 93, 2439-2461.
68. Norrby, P.-O.; Brandt, P.; Rein, T. J. Org. Chem. 1999, 64, 5845-5852.
69. (a) Norrby, P.-O.; Rasmussen, T.; Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 10186-10192.
70. (b) Fristrup, P.; Tanner, D.; Norrby, P.-O. Chirality 2003, 15, 360-368.
71. Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551-8566.
72. 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.
73. Norrby, P.-O. In Molecular Mechanics as a Predictive Tool in Asymmetric Catalysis; Truhlar, D. G., Morokuma, K., Eds.; American Chemical Society: Washington, DC, 1999; pp 163-172.
74. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361-373.
75. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
76. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
77. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. 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. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
78. Norrby, P.-O.; Liljefors, T. J. Comput. Chem. 1998, 19, 1146-1166.
79. (a) Norrby, P.-O.; Brandt, P. Coord. Chem. Rev. 2001, 212, 79-109.
80. (b) Norrby, P.-O. Recipe for an Organometallic Force Field. In Computational Organometallic Chemistry; Cundari, T., Ed.; Marcel Dekker: New York, 2001; pp 7-37.
81. 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.
82. Allinger, N. L.; Zhou, X.; Bergsma, J. J. Mol. Struct. (THEOCHEM) 1994, 312, 69-83.
83. Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110-1117.
84. Kolossvary, I.; Guida, W. C. J. Am. Chem. Soc. 1996, 118, 5011-5019.
85. The Low Mode method can invert chiral atoms, and the automatic chirality check implemented in MacroModel v. 6.0 to avoid this inversion cannot handle the almost planar atom, which is responsible for the forming chirality. Hence, filtering is usually required after the Low Mode search, to ensure that only the desired forming chirality is present.
86. The LACVP* basis set uses 6-31G* for light elements and the Hay - Wadt ECP for Zn: Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
87. http://www.schrodinger.com.
88. (a) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2761-2771.
89. (b) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007-2015.
90. Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712-7713.
91. Rasmussen, T.; Dölker, N.; Maseras, F.; Norrby, P.-O., manuscript in preparation.