Magnesium coordination-directed N-selective stereospecific alkylation of 2-pyridones, carbamates, and amides using α-halocarboxylic acids

Journal of the American Chemical Society

Volumn 132, Issue 44, 2010, Pages 15525-15527

  Fang, Yuan Qing ^a   Bio, Matthew M ^a   Hansen, Karl B ^a   Potter, Matthew S ^a   Clausen, Andrew ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-PYRIDONES; CHEMICAL YIELDS; STEREOSPECIFIC;

AMIDES; CARBOXYLATION; CARBOXYLIC ACIDS; COORDINATION REACTIONS; MAGNESIUM; REACTION INTERMEDIATES;

ALKYLATION;

2 PYRIDONE DERIVATIVE; ALPHA HALOCARBOXYLIC ACID; AMIDE; CARBAMIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; MAGNESIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; CRYSTALLIZATION; MOLECULAR MECHANICS; STEREOSPECIFICITY; SUBSTITUTION REACTION;

ALKYLATION; AMIDES; CARBAMATES; CARBOXYLIC ACIDS; HALOGENS; HYDROCARBONS, HALOGENATED; MAGNESIUM; MOLECULAR STRUCTURE; PYRIDONES; STEREOISOMERISM;

EID: 78149265962     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107709w     Document Type: Article

References (34)

1. Carreira, E. M. and Kvaerno, L. Classics in Stereoselective Synthesis; Wiley-VCH: Weinheim, 2009.
2. Johnson, N. B., Lennon, I. C., Moran, P. H., and Ramsden, J. A. Acc. Chem. Res. 2007, 40, 1291
3. Chiral chloroacid 5 (92-97%ee) is commercially available at <100/kg on manufacturing scale. Preparation of various chiral chloroacids from natural amino acids: Koppenhoefer, B. and Schurig1, V. Org. Synth. Coll. Vol. 8 1993, 119
4. Amatore, M., Beeson, T. D., Brown, S. P., and MacMillan, D. W. C. Angew. Chem., Int. Ed. 2009, 48, 5121 and references therein
5. Vora, H. U. and Rovis, T. J. Am. Chem. Soc. 2010, 132, 2860
6. Golec, J., Charifson, P., Charrier, J.-D., and Binch, H. WO01042216, 2001.
7. Pfefferkorn, J. A. Bioorg. Med. Chem. Lett. 2009, 19, 3247
8. Sellstedt, M. and Almqvist, F. Org. Lett. 2009, 11, 5470
9. Hunt, A. H., Mynderse, J. S., Samlaska, S. K., Fukuda, D. S., Maciak, G. M., Kirst, H. A., Occolowitz, J. L., Swartzendruber, J. K., and Jones, N. D. J. Antibiot. 1988, 41, 771
10. Dragovich, P. S. J. Med. Chem. 2003, 46, 4572
11. Minich, M. L., Watson, I. D., Filipski, K. J., and Pfefferkorn, J. A. Tetrahedron Lett. 2009, 50, 2094
12. Martinez, C. A., Yazbeck, D. R., and Tao, J. Tetrahedron 2004, 60, 759
13. Verissimo, E., Berry, N., Gibbons, P., Cristiano, M. L. S., Rosenthal, P. J., Gut, J., Ward, S. A., and O'Neill, P. M. Bioorg. Med. Chem. Lett. 2008, 18, 4210
14. Rodrigues, A., Lee, E. E., and Batey, R. A. Org. Lett. 2010, 12, 260
15. Babic, A. and Pecar, S. Tetrahedron: Asymmetry 2008, 19, 2265
16. Zhang, Y.-H., Gao, Z.-X., Zhong, C.-L., Zhou, H.-B., Chen, L., Wu, W.-M., Peng, X.-J., and Yao, Z.-J. Tetrahedron 2007, 63, 6813
17. Ueda, T., Feng, F., Sadamoto, R., Niikura, K., Monde, K., and Nishimura, S.-I. Org. Lett. 2004, 6, 1753
18. Houpis, I. N., Patterson, L. E., Alt, C. A., Rizzo, J. R., Zhang, T. Y., and Haurez, M. Org. Lett. 2005, 7, 1947
19. Aikins, J. A., Haurez, M., Rizzo, J. R., Van Hoeck, J.-P., Brione, W., Kestemont, J.-P., Stevens, C., Lemair, X., Stephenson, G. A., Marlot, E., Forst, M., and Houpis, I. N. J. Org. Chem. 2005, 70, 4695
20. Chung, N. M. and Tieckelmann, H. J. Org. Chem. 1970, 35, 2517
21. Liu, H., Ko., S.-B., Josien, H., and Curran, D. P. Tetrahedron Lett. 1995, 36, 8917
22. Clayton, J., Greeves, N., Warren, S., and Wothers, P. Organic Chemistry; Oxford University Press: New York, 2001; pp, 971 - 972.
23. Product 2 completely racemizes with excess MO t -Bu (M = Li, Na, K) in THF at 60 °C.
24. 2O is necessary for this high reactivity.
25. Boussac, H., Crassous, J., Dutasta, J.-P., Grosvalet, L., and Thozet, A. Tetrahedron: Asymmetry 2002, 13, 975
26. Holtz, H. D. and Stock, L. M. J. Am. Chem. Soc. 1976, 87, 2404
27. Arcoria, A. and Fisichella, S. Tetrahedron Lett. 1971, 3347
28. Kirby, A. J. Adv. Phys. Org. Chem. 1981, 17, 183
29. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734
30. Anslyn, E. V. and Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2004; pp 496 - 497.
31. Stork, G. and Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595
32. The O -coordination structure of 2-pyridone magnesium complexes has been well characterized by X-ray single crystallography in the literature.
33. Blake, A. J., Gould, R. O., Grant, C. M., Milne, P. E. Y., Reed, D., and Winpenny, R. E. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 195
34. Nichol, G. S. and Clegg, W. Inorg. Chim. Acta 2006, 359, 3474