Increasing enantioselectivities and reactivities by stereochemical tuning: Fenchone-based catalysts in dialkylzinc additions to benzaldehyde

European Journal of Organic Chemistry

Volumn , Issue 9, 2000, Pages 1785-1792

  Goldfuss, Bernd ^a   Steigelmann, Melanie ^a   Rominger, Frank ^b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b NONE

Author keywords

Asymmetric synthesis; QM MM computations; Transition structures; Zinc

Indexed keywords

BENZALDEHYDE; ZINC DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034031069     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200005)2000:9<1785::AID-EJOC1785>3.0.CO;2-0     Document Type: Article

References (57)

1. For applications of organozinc reagents in organic synthesis see: [1a] P. Knochel, F. Langer, A. Longeneau, M. Rottländer, T. Stüdemann, Chem. Ber. 1997, 130, 1021-1027. -
2. [1b] P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188.
3. [2a] A. Thompson, E. G. Corley, M. F. Huntington, E. J. J. Grabowski, J. F. Remenar, D. B. Collum, J. Am. Chem. Soc. 1998, 120, 2028-2038. -
4. [2b] M. E. Pierce, R. L. Parsons, Jr., L. A. Radesca, Y. S. Lo, S. Silverman, J. R. Moore, Q. Islam, A. Choudhury, J. M. D. Fortunak, D. Nguyen, C. Luo, S. J. Morgan, W. P. Davis, P. N. Confalone, C. Chen, R. D. Tillyer, L. Frey, L. Tan, F. Xu, D. Zhao, A. S. Thompson, E. G. Corley, E. J. J. Grabowski, R. Reamer, P. J. Reider, J. Org. Chem. 1998, 63, 8536-8543.
5. [3a] M. Arend, Angew. Chem. 1999, 111, 3047-3049; Angew. Chem. Int. Ed. 1999, 38, 2873-2874. -
6. [3a] M. Arend, Angew. Chem. 1999, 111, 3047-3049; Angew. Chem. Int. Ed. 1999, 38, 2873-2874. -
7. [3b] P. Brandt, C. Hedberg, K. Lawonn, P. Pinho, P. G. Andersson, Chem. Eur. J. 1999, 5, 1692-1699. -
8. [3c] S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094. -
9. [3d] D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 5, 1895-1946.
10. [4a] Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), vol. I-III, Springer, Heidelberg, 1999. -
11. [4b] G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (Eds.), Methods Org. Chem. (Houben-Weyl), 1996, vol. E21b.
12. For reviews see: [5a] K. Soai, S. Niwa, Chem. Rev. 1992, 92, 835-856 -
13. [5b] R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69. -
14. [5b] R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69. -
15. [5c] D. A. Evans, Science 1998, 22, 420-426.
16. Ferrocenyl-hydroxy-oxazolines: [6a] C. Bolm, K. Muniz, Chem. Commun. 1999, 1295-1296. -
17. [6b] C. Bolm, K. Muniz-Fernandez, A. Seger, G. Raabe, K. Günther, J. Org. Chem. 1998, 63, 7860-7867. - Arene chromium ligands:
18. [6c] C. Bolm, K. Muniz, Chem. Soc. Rev. 1999, 28, 51-59. - Titanium TADDOLates:
19. [6d] P. B. Rheiner, D. Seebach, Chem. Eur. J. 1999, 5, 3221-3236. -
20. [6e] B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 100-101; Angew. Chem. Int. Ed. Engl. 1991, 30, 99-101. -
21. [6e] B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 100-101; Angew. Chem. Int. Ed. Engl. 1991, 30, 99-101. -
22. [6f] B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 1383-1385; Angew. Chem. Int. Ed. Engl. 1991, 30, 1321-1323.
23. [6f] B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 1383-1385; Angew. Chem. Int. Ed. Engl. 1991, 30, 1321-1323.
24. [7a] J. Eriksson, P. I. Arvidsson, Ö. Davidsson, Chem. Eur. J. 1999, 5, 2356-2361. -
25. [7b] O. Juanes, J. C. Rodriguez-Ubis, E. Brunet, H. Pennemann, M. Kossenjans, J. Martens, Eur. J. Org. Chem. 1999, 3323-3333.
26. B. Goldfuss, K. N. Houk, J. Org. Chem. 1998, 63, 8998-9006.
27. [9a] H.-U. Blaser, Chem. Rev. 1992, 92, 935-952. -
28. [9b] M. Genov, K. Kostova, V. Dimitrov, Tetrahedron: Asymmetry 1997, 8, 1869-1876. -
29. [9c] Y. Suzuki, Y. Ogata, K. Hiroi, Tetrahedron: Asymmetry 1999, 10, 1219-1222.
30. [10a] M. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028-4036. -
31. [10b] M. Kitamura, S. Suga, K. Kawai, R. Noyori, J. Am. Chem. Soc. 1986, 108, 6071-6072.
32. [11a] G. Helmchen, J. Organomet. Chem. 1999, 576, 203-214. -
33. [11b] A. Pfaltz, Synlett 1999, 835-842. -
34. [11c] J. M. J. Williams, Synlett 1996, 705-710. -
35. [11d] B. M. Trost, D. L. V. Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327-9343.
36. Aminoarenethiolate ligands with similar benzylamino groups were successfully employed by the van Koten group in enantioselective diethylzinc additions: E. Rijnberg, N. J. Hovestad, A. W. Kleij, J. T. B. H. Jastrzebski, J. Boersma, M. D. Janssen, A. L. Spek, G. van Koten, Organometallics 1997, 16, 2847-2857.
37. B. Goldfuss, M. Steigelmann, S. I. Kahn, K. N. Houk, J. Org. Chem., 2000, 65, 77-82.
38. For effects of trialkylsilyl substituents in palladium-catalyzed enantioselective rearrangements of allylic imidates and in cross-couplings see: [14a] Y. Donde, L. E. Overman J. Am. Chem. Soc. 1999, 121, 2933-3934. -
39. [14b] J. M. Brown, M. Pearson, J. T. B. H. Jastrzebski, G. van Koten, J. Chem. Soc., Chem. Commun. 1992, 1440-1441.
40. The N7-C6-C5-C8 angle in the X-ray crystal structure of 4 (110°) is not increased relative to that in the X-ray crystal structure of 2 (110°) because close C6H-HCSi9 distances (H H: 2.05 Å, C-C: 3.48 Å) favor a small N7-C6-C5-C8 dihedral angle in 4. The repulsive C6H-HCSi9 contacts would decrease even more if N7-C6-C5-C8 increased to over 110°. Trimethylsilyl conformations analogous to that in the X-ray crystal structure of 4 were examined in transition structures with 4, but were found to be energetically unfavorable.
41. For correlations of ligand bite angles and catalyst reactivity see-[16a] P. Dierkes, P. W. N. M. van Leeuwen, J. Chem. Soc., Dalton Trans. 1999, 1519-1529. -
42. [16b] R. J. van Haaren, H. Oevering, B. B. Coussens, G. P. F. van Strijdonck, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Eur. J. Inorg. Chem. 1999, 1237-1241.
43. M. Kitamura, H. Oka, R. Noyori, Tetrahedron 1999, 55, 3605-3614.
44. [18a] M. Kitamura, S. Suga, H. Oka, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800-9809. -
45. [18b] M. Kitamura, M. Yamakawa, H. Oka, S. Suga, R. Noyori, Chem. Eur. J. 1996, 2, 1173-1181.
46. B. Goldfuss, S. I. Kahn, K. N. Houk, Organometallics 1999, 18, 2927-2929.
47. For both 1-Zn and 3-Zn, syn dimers were computed [ONIOM (RHF/LanL2DZ:UFF)] to be most stable and hence were considered for the monomer-dimer equilibrium; anti dimers, with anti aligned methyl groups at zinc centers, were computed to be 4.7 kcal/mol (1-Zn) and 3.4 kcal/mol (3-Zn) higher in energy.
48. Attempts to obtain X-ray crystal structures of analogous methylzinc complexes of ligands 2 and 4 were not successful so far. No stable dimeric methylzinc complexes were found computationally for ligands 2 or 4.
49. Increased reactivity can lead to increased enantioselectivity, due to a smaller contribution of the slower, uncatalyzed racemic side reaction of diethylzinc with benzaldehyde. This, however, cannot explain the change in the direction of enantioselectivity for 3 relative to 1.
50. [23a] M. Yamakawa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 6327-6335. -
51. [23b] M. Yamakawa, R. Noyori, Organometallics 1999, 18, 128-133.
52. L. Brandsma, H. Verkruijsse, Preparative Polar Organometallic Chemistry, Springer, Heidelberg, 1987.
53. S. Dapprich, I. Komaromi, K. S. Byun, K. Morokuma, M. J. Frisch, Theochem. 1999, 461-462, 1-21.
54. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.5, Gaussian, Inc., Pittsburgh, PA. 1998.
55. A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard III, W. M. Skiff, J. Am. Chem. Soc. 1992, 114, 10024-10035.
56. P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 270.
57. T. H. Dunning Jr., P. J. Hay, in Modern Theoretical Chemistry (Ed.: H. F. Schaefer III) Plenum, New York, 1976, vol. 3, p. 1.