An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation

Journal of Organic Chemistry

Volumn 68, Issue 14, 2003, Pages 5731-5734

  Burk, Mark J ^a,d   De Koning, Pieter D ^a   Grote, Todd M ^b   Hoekstra, Marvin S ^b   Hoge, Garrett ^c   Jennings, Rex A ^b   Kissel, William S ^b   Le, Tung V ^b   Lennon, Ian C ^a   Mulhern, Thomas A ^b   Ramsden, James A ^a   Wade, Robert A ^b  

^a DOW CHEMICAL COMPANY   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^c PFIZER INC   (United States)

^d DIVERSA CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; HYDROGENATION; NICKEL; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVE SYNTHESIS;

AROMATIC HYDROCARBONS;

ANTICONVULSIVE AGENT; PREGABALIN;

ARTICLE; CATALYST; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; REACTION ANALYSIS;

ANTICONVULSANTS; BACTERIAL PROTEINS; GAMMA-AMINOBUTYRIC ACID; HYDROGENATION; STEREOISOMERISM; TRANSCRIPTION FACTORS;

EID: 10744227163     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034397b     Document Type: Article

References (14)

1. Yuen, P.; Kanter, G. D.; Taylor, C. P.; Vartanian, M. G. Bioorg. Med. Chem. Lett. 1994, 4, 823.
2. Hoekstra, M. S.; Sobieray, D. M.; Schwindt, M. A.; Mulhern, T. A.; Grote, T. M.; Huckabee, B. K.; Hendrickson, V. S.; Franklin, L. C.; Granger E. J.; Karrick, G. L. Org. Proc. Res. Dev. 1997, 1, 26.
3. (a) Jendrella, H.; Henning, R.; Seuring, B.; Herchen, J.; Kulitzscher, B.; Wunner, J. Synlett 1993, 155.
4. (b) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron 1993, 49, 1793.
5. (c) Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. 1998, 37, 1931.
6. (a) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571.
7. (b) Shao, L.; Miyata, S.; Muramatsu, H.; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Perkin Trans. 1 1990, 1441.
8. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.
9. Burk, M. J.; Goel, O. P.; Hoekstra, M. S.; Mich, T. F.; Mulhern, T. A.; Ramsden, J. A. Warner-Lambert Company, WO 01/55090 A1, 2001; Chem. Abstr. 2001, 135, 122750.
10. Yamamoto, K.; Deguchi, R.; Tsuji, J. Bull. Chem. Soc. Jpn. 1985, 58, 3397.
11. Basaviah, D.; Gowriswari, V. V. L. Synth. Commun. 1987, 17, 587.
12. Burk, M. J.; Bienwald, F.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64, 3290.
13. Berens, U.; Burk, M. J.; Gerlach, A.; Hems, W. Angew. Chem., Int. Ed. 2000, 39, 1981.
14. Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746.