An enantioselective route to α-methyl carboxylic acids via metal and enzyme catalysis

Organic Letters

Volumn 9, Issue 24, 2007, Pages 5095-5098

  Norinder, Jakob ^a   Bogár, Krisztián ^a   Kanupp, Lisa ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CARBOXYLIC ACID; COPPER; LIPASE B, CANDIDA ANTARCTICA; PROPANOL; RUTHENIUM; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS;

CARBOXYLIC ACIDS; CATALYSIS; COPPER; KINETICS; LIPASE; MOLECULAR STRUCTURE; PROPANOLS; RUTHENIUM; STEREOISOMERISM;

EID: 36849048729     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702261t     Document Type: Article

References (33)

1. (a) Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321.
2. (b) Pàmies, O.; Bäckvall, J.-E. Chem. Rev. 2003, 103, 3247.
3. (c) Pàmies, O.; Bäckvall, J.-E. Trends Biotechnol. 2004, 3, 130.
4. (d) Kim, M.-J.; Ahn, Y.; Park, J. Curr. Opin. Biotechnol. 2002, 13, 578.
5. Erratum: Kim, M.-J.; Ahn, Y.; Park, J. Curr. Opin. Biotechnol. 2003, 14, 131.
6. (e) Pellissier, H. Tetrahedron 2003, 59, 8291.
7. (a) Csjernyik, G.; Bogár, K.; Bäckvall, J.-E. Tetrahedron Lett. 2004, 45, 6799.
8. (b) Martín-Matute, B.; Edin, M.; Bogár, K.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2004, 43, 6535.
9. (c) Martín-Matute, B.; Edin, M.; Bogár, K.; Kaynak, F. B.; Bäckvall, J.-E. J. Am. Chem. Soc 2005, 127, 8817.
10. (d) Martín-Matute, B.; Ãberg, J. B.; Edin, M.; Bäckvall, J.-E. Chem. Eur. J. 2007, 13, 6063.
11. (a) Borén, L.; Martin-Matute, B.; Xu, Y.; Cordova, A.; Bäckvall, J.-E. Chem. Eur. J. 2006, 12, 225.
12. (b) Bogár, K.; Hoyos Vidal, P.; Alcántara León, A. R.; Bäckvall, J.-E. Org. Lett. 2007, 9, 3401.
13. (a) Trost, B. M.; Klun, T. P. J. Org. Chem. 1980, 45, 4256.
14. (b) Ibuka, T.; Akimoto, N.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Org. Chem. 1989, 54, 4055.
15. (c) Belelie, J. L.; Chong, J. M. J. Org. Chem. 2001, 66, 5552.
16. (d) Breit, B.; Demel, P.; Studte, C Angew. Chem., Int. Ed. 2004, 43, 3786.
17. (e) Calaza, M. I.; Yang, X.; Soorukram, D.; Knochel, P. Org. Lett. 2004, 6, 529.
18. (f) Harrington-Frost, N.; Leuser, H.; Calaza, M. I.; Kneisel, F. F.; Knochel, P. Org. Lett. 2003, 5, 2111.
19. Goering, L. H.; Tseng, C. C. J. Org. Chem. 1983, 48, 3986.
20. (a) Goering, L. H.; Singleton, V. D., Jr. J. Org. Chem. 1983, 48, 1531.
21. (b) Goering, L. H.; Kantner, S. S. J. Org. Chem. 1983, 48, 721.
22. (c) Goering, L. H.; Kantner, S. S. J. Org. Chem. 1981, 46, 2144.
23. (d) Goering, L. H.; Singleton, V. D., Jr. J. Am. Chem. Soc. 1976, 98, 7854.
24. (e) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1994, 59, 4126.
25. (a) Bäckvall, J.-E.; Sellen, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615.
26. (b) Bäckvall, J.-E.; Sellén, M. J. Chem. Soc., Chem. Commun. 1987, 827.
27. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063.
28. Norinder, J.; Bäckvall, J.-E. Chem. Eur. J. 2007, 13, 4094.
29. Martin-Matute, B.; Bogar, K.; Edin, M.; Kaynak, F. B.; Bäckvall, J.-E. Chem. Eur. J. 2005, 11, 5832.
30. Kim, M.-J.; Chung, Y. I.; Choi, Y. K.; Lee, H. K.; Kim, D.; Park, J. J. Am. Chem. Soc. 2003, 125, 11494.
31. 2 gave essentially the same stereo- and regioselectivity as well as yields.
32. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
33. Guintchin, B.; Bienz, S. Tetrahedron 2003, 59, 7527.