Dynamic Kinetic Resolution for Asymmetric Synthesis of α-Alkyl Amino Acids via Dual-Function Catalysis of Modified Cinchona Alkaloids

Synlett

Volumn , Issue 12, 2003, Pages 1927-1930

  Hang, Jianfeng ^a   Deng, Li ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

Amino acids; Cinchona alkaloid; Dynamic kinetic resolution; Kinetic resolution; Racemization

Indexed keywords

AMINO ACID; CINCHONA ALKALOID;

ALCOHOL OXIDATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CRYSTALLIZATION; ELECTRON TRANSPORT; KINETICS;

EID: 0142059747     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41500     Document Type: Article

References (18)

1. Reviews on dynamic kinetic resolutions: (a) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407. (b) Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321. (c) Faber, K. Chem.-Eur. J. 2001, 7, 5005. (d) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (e) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (f) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
2. Reviews on dynamic kinetic resolutions: (a) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407. (b) Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321. (c) Faber, K. Chem.-Eur. J. 2001, 7, 5005. (d) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (e) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (f) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
3. Reviews on dynamic kinetic resolutions: (a) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407. (b) Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321. (c) Faber, K. Chem.-Eur. J. 2001, 7, 5005. (d) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (e) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (f) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
4. Reviews on dynamic kinetic resolutions: (a) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407. (b) Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321. (c) Faber, K. Chem.-Eur. J. 2001, 7, 5005. (d) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (e) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (f) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
5. Reviews on dynamic kinetic resolutions: (a) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407. (b) Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321. (c) Faber, K. Chem.-Eur. J. 2001, 7, 5005. (d) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (e) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (f) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
6. Reviews on dynamic kinetic resolutions: (a) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407. (b) Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321. (c) Faber, K. Chem.-Eur. J. 2001, 7, 5005. (d) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (e) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (f) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
7. (a) Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892.
8. (b) Liang, J.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1998, 63, 3154.
9. (c) Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
10. (d) Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937.
11. (e) Persson, B. A.; Larsson, A. L. E.; Le Ray, M.; Bäckvall, J.-E. J. Am. Chem. Soc. 1999, 121, 1645.
12. (a) Hang, J.; Tian, S.-K.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2001, 123, 12696.
13. (b) Hang, J.; Li, H.; Deng, L. Org. Lett. 2002, 4, 3321.
14. Tang, L.; Deng, L. J. Am. Chem. Soc. 2002, 124, 2870.
15. Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965.
16. Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144.
17. 2: 306.9473, found: 306.9472.
18. 2: 322.0071, found: 322.0061. Compound 2h (55.8 mg, 75% ee) was recrystallized from EtOAc (0.30 mL) and hexanes (1.0 mL) to give a white solid (34.3 mg, 53% yield from 1h, 99.4% ee).