A short enantioselective synthesis of N-boc-(2R,3R)-3-methyl-3- hydroxypipecolic acid from geraniol

Journal of Organic Chemistry

Volumn 73, Issue 8, 2008, Pages 3295-3298

  Noe, Mark C ^a   Hawkins, Joel M ^a   Snow, Sheri L ^a   Wolf Gouveia, Lilli ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE SYNTHESIS; SHARPLESS ASYMMETRIC EPOXIDATION;

CHIRALITY; ENANTIOSELECTIVITY; EPOXIDATION; SYNTHESIS (CHEMICAL);

ORGANIC ACIDS;

3 METHYL 3 HYDROXYPIPECOLIC ACID DERIVATIVE; AGGRECANASE; ALKENE DERIVATIVE; COLLAGENASE 3; GERANIOL; MATRIX METALLOPROTEINASE INHIBITOR; PIPECOLIC ACID DERIVATIVE; PIPERIDINE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; ENANTIOMER; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; SHARPLESS EPOXIDATION; STEREOCHEMISTRY;

HYDROLYSIS; MOLECULAR STRUCTURE; OZONE; PIPECOLIC ACIDS; STEREOISOMERISM; TERPENES;

EID: 42149102722     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800080t     Document Type: Article

References (22)

1. Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 109, 5031-5033.
2. Kawai, M.; Pottorf, R. S.; Rich, D. H. J. Med. Chem. 1986, 29, 2409-2411.
3. Hanessian, S.; M-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
4. Ferreira, F.; Greck, C.; Genet, J. P. Bull. Soc. Chim. Fr. 1997, 134, 615-621.
5. Noe, M. C.; Letavic, M. A.; Hawkins, J. M. Eur. Pat. Appl. EP 1081137 A1, 2001.
6. Greck, C.; Ferreira, F.; Genet, J. P. Tetrahedron Lett. 1996, 37, 2031-2034.
7. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866-1875.
8. Knight, D. W.; Lewis, N.; Share, A. C.; Haigh, D. Tetrahedron: Asymmetry 1993, 4, 625-628.
9. Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Gasparri, Fava, G.; Belichi Ferrari, M.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975-2987.
10. For other methods of producing 3- and 4-hydroxypipecolic acid, see: (a) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551-3553.
11. (b) Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Gasparri Fava, G.; Belicchi Ferrari, M.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975-2987.
12. (c) Kumar, P.; Bodas, M. J. Org. Chem. 2005, 70, 360-363.
13. (d) Liang, N.; Datta, A. J. Org. Chem. 2005, 70, 10182-10185.
14. (e) Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002.
15. (f) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 2001, 42, 5223-5225.
16. (g) Bodas, M. S.; Kumar, P. Tetrahedron Lett. 2004, 45, 8461-8463.
17. (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846.
18. (i) Kadouri-Puchot, C.; Cornesse, S. Amino Acids 2005, 29, 101-130 and references cited therein.
19. Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922-1925.
20. Roush, W. R.; Adam, M. A. J. Org. Chem. 1985, 50, 3752-3757.
21. Bernotas, R.; Ganem, B. J. Org. Chem. 1987, 52, 312-316.
22. Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564-2566.