Enantioselective borodeuteride reduction of aldimines catalyzed by cobalt complexes: Preparation of optically active deuterated primary amines

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3555-3558

  Miyazaki, Daichi ^a   Nomura, Kohei ^a   Yamashita, Tatsuya ^a   Iwakura, Izumi ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; COBALT COMPLEX; DEUTERIDE; RADIOISOTOPE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DEPROTECTION REACTION; ENANTIOSELECTIVITY; ISOTOPE LABELING; REDUCTION; STEREOCHEMISTRY;

EID: 0142074849     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0349920     Document Type: Article

References (36)

1. (a) Stille, J. K.; Lau, K. S. Y. J. Am. Chem. Soc. 1976, 98, 5832-5840.
2. (b) Parry, R. J.; Trinor, D. A. J. Am. Chem. Soc. 1978, 100, 5243-5244.
3. (c) Shibuya, M.; Chou, H.-M.; Fountoulakis, M.; Hassam, S.; Kim, S.-U.; Kobayashi, K.; Otsuka, H.; Rogalska, E.; Casssady, J. M.; Floss, H. G. J. Am. Chem. Soc. 1990, 112, 297-304.
4. (d) Mu, Y.-Q.; Omer, C. A.; Gibbs, R. A. J. Am. Chem. Soc. 1996, 118, 1818-1823.
5. (a) Lown, J. W.; Akhtar, M. H. J. Chem. Soc., Chem. Commun. 1973, 511-513.
6. (b) Battersby, A. R.; Staunton, J.; Summers, M. C. J. Chem. Soc., Perkin Trans. 1 1976, 1052-1056.
7. (c) Meyers, A. I.; Dickman, D. A. J. Am. Chem. Soc. 1987, 109, 1263-1265.
8. (a) Streitwieser, A.; Wolfe. J. R. J. Org. Chem. 1963, 28, 3263-3264.
9. (b) Hammerschmidt, F.; Hanbauer, M. J. Org. Chem. 2000, 65, 6121-6131.
10. (a) Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145-2147.
11. (b) Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1996, 737-738.
12. (c) Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1996, 1081-1082.
13. (d) Nagata, T.; Sugi, K. D.; Yamada, T.; Mukaiyama, T. Synlett 1996, 1076-1078.
14. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493-494.
15. Miyazaki, D.; Nomura, K.; Ichihara, H.; Ohtsuka, Y.; Ikeno, T.; Yamada, T. New J. Chem. 2003, 27, 1164-1166.
16. For the borodeuteride reduction of the aldehyde, employing THFA resulted in decreasing the isotopic purity of the corresponding alcohol because the deuteride of sodium borodeuteride could be exchanged with a proton from the alcohol: (a) Cornforth, R. H. Tetrahedron 1970, 26, 4635-4640. (b) Davis, R. E. ; Bromels, E.; Kibby, C. L. J. Am. Chem. Soc. 1962, 84, 885-892. Therefore, THFA-d was prepared and employed for the borodeuteride modification instead of THFA, and the product was obtained with a >95% deuteration degree.
17. For the borodeuteride reduction of the aldehyde, employing THFA resulted in decreasing the isotopic purity of the corresponding alcohol because the deuteride of sodium borodeuteride could be exchanged with a proton from the alcohol: (a) Cornforth, R. H. Tetrahedron 1970, 26, 4635-4640. (b) Davis, R. E. ; Bromels, E.; Kibby, C. L. J. Am. Chem. Soc. 1962, 84, 885-892. Therefore, THFA-d was prepared and employed for the borodeuteride modification instead of THFA, and the product was obtained with a >95% deuteration degree.
18. 2 in THF (Fujihara, H.; Nagai, K.; Tomioka, K. J. Am. Chem. Soc. 2000, 122, 12055-12056). It was, however, found that the degree of deuteration of the products decreased through both deprotection processes.
19. (a) Hutchins, R. O.; Abdel-Magid, A.; Stercho, Y. P.; Wambsgans, A. J. Org. Chem. 1987, 52, 704-706.
20. (b) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097-1098.
21. Greene, T. W.; Wuts, P. G. Protective Group in Organic Synthesis; John Wiley & Sons: New York, 1999; p 598.
22. (a) Ichikawa, A.; Hiradate, S.; Sugio, A.; Kuwahara, S.; Watanabe, M.; Harada, N. Tetarahedron: Asymmetry 1999, 10, 4075-4078.
23. (b) Harada, N.; Watanabe, M.; Kuwahara, S.; Sugio, A.; Kasai, Y.; Ichikawa, A. Tetarahedron: Asymmetry 2000, 11, 1249-1253.
24. Catalysts employed all appeared in the following report: Ohtsuka, Y.; Koyasu, K.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 2543-2546.
25. Cobalt-hydride was assumed to be the reactive intermediate in the borohydride reduction catalyzed by the optically active β-ketoiminato cobalt complexes and was recently detected by FAB mass analysis: Ohtsuka, Y.; Ikeno, T.; Yamada, T. Tetrahedron: Asymmetry 2003, 14, 967-970.
26. (a) Tolman, C. A. Chem. Rev. 1977, 77, 317-348.
27. (b) White, D.; Coville, N. J. Adv. Organomet. Chem. 1994, 36, 95-158.
28. Yamada, T.; Nagata, T.; Sugi, K. D.; Yorozu, K.; Ikeno, T.; Ohtsuka, Y.; Miyazaki, D.; Mukaiyama, T. Chem. Eur. J. 2003, 9, in print.
29. (a) Ohba, S.; Nagata, T.; Yamada, T. Acta Crystallogr. E 2001, m124-m126.
30. (b) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342.
31. (c) Kezuka, S.; Kogami, Y.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2003, 76, 49-58.
32. Observation that the aryl ketones were reduced faster than the alkyl ketones could be explained similarly by π-π interaction between the substrate and cobalt complex. Ohtsuka, Y.; Koyasu, K.; Miyazaki, D.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 3421-3424.
33. Diphenylphosphinyl imine of tetralone could not be reduced in the enantioselective borohydride reduction catalyzed by the cobalt complex 1. See ref 5.
34. Theoretical analysis of the structures of diphenylphosphinyl aldimine and ketimine was performed using the B3LYP method with 6-31G* as basis sets. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652. (b) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. (c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Rohb, 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
35. Theoretical analysis of the structures of diphenylphosphinyl aldimine and ketimine was performed using the B3LYP method with 6-31G* as basis sets. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652. (b) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. (c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Rohb, 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
36. Theoretical analysis of the structures of diphenylphosphinyl aldimine and ketimine was performed using the B3LYP method with 6-31G* as basis sets. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652. (b) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. (c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Rohb, 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.