Obtaining enriched compounds via a tandem enantioselective reaction and kinetic resolution polishing sequence

Journal of Organic Chemistry

Volumn 77, Issue 7, 2012, Pages 3570-3575

  Klauck, Maggie I ^a   Patel, Sachin G ^a   Wiskur, Sheryl L ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE REACTIONS; KINETIC RESOLUTION; NONENZYMATIC KINETIC RESOLUTIONS;

ALDEHYDES; KETONES; ORGANIC COMPOUNDS;

KINETICS;

ALCOHOL; ALDEHYDE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 84859597744     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202653b     Document Type: Article

References (26)

1. Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H, Eds.; John Wiley & Sons, Inc.: New York, 1988; Vol. 18, pp 249-330.
2. Spivey, A. C.; Maddaford, A.; Redgrave, A. J. Org. Prep. Proced. Int. 2000, 32, 331-365
3. Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26
4. Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407-1446
5. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974-4001
6. For a review, see: Fransson, L.; Moberg, C. Chem. Cat. Chem. 2010, 2, 1523-1532
7. Wieser, M.; Nagasawa, T. Stereoselective Nitrile-Converting Enzymes. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, Inc.: New York, 2000; pp 461-486.
8. Rowe, B. J.; Spilling, C. D. Tetrahedron: Asymmetry 2001, 12, 1701-1708
9. Edin, M.; Bäckvall, J.-E.; Córdova, A. Tetrahedron Lett. 2004, 45, 7697-7701
10. Belokon, Y. N.; Blacker, A. J.; Clutterbuck, L. A.; Hogg, D.; North, M.; Reeves, C. Eur. J. Org. Chem. 2006, 4609-4617
11. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553
12. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C. P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926
13. Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 1996, 61, 3214-3217
14. Salunkhe, A. M.; Burkhardt, E. R. Tetrahedron Lett. 1997, 38, 1523-1526
15. Cho, B. T.; Choi, O. K.; Kim, D. J. Tetrahedron: Asymmetry 2002, 13, 697-703
16. Garrett, C. E.; Prasad, K.; Repić, O.; Blacklock, T. J. Tetrahedron: Asymmetry 2002, 13, 1347-1349
17. Huertas, R. E.; Corella, J. A.; Soderquist, J. A. Tetrahedron Lett. 2003, 44, 4435-4437
18. Wang, X.; Du, J.; Liu, H.; Du, D. M.; Xu, J. Heteroatom. Chem. 2007, 18, 740-746
19. Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351-1354
20. Horeau, A. Tetrahedron 1975, 31, 1307-1309
21. Gawley, R. E. J. Org. Chem. 2006, 71, 2411-2416
22. p). See: Kanamori, Y.; Watanabe, M.; Kawauchi, K.; Chen, Y.-G.; Yanagishita, H.; Hirata, H. J. Oleo Sci. 2005, 54, 21-31
23. Sheppard, C. I; Taylor, Jessica, L.; Wiskur, S. L. Org. Lett. 2011, 13, 3794-3797
24. Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092-2093
25. Trost, B. M.; Dong, G. J. Am. Chem. Soc. 2010, 132, 16403-16416
26. Absolute chirality of 6 determined by HPLC and compared to known separation on a Chiralcel OD-H column: Jain, P.; Antilla, J. C. J. Am. Chem. Soc. 2010, 132, 11884