Origin of enantioselectivity in benzotetramisole-catalyzed dynamic kinetic resolution of azlactones

Organic Letters

Volumn 14, Issue 13, 2012, Pages 3288-3291

  Liu, Peng ^a   Yang, Xing ^b   Birman, Vladimir B ^b   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTETRAMISOLE; DRUG DERIVATIVE; LACTONE; TETRAMISOLE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; QUANTUM THEORY; STEREOISOMERISM;

CATALYSIS; KINETICS; LACTONES; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM; TETRAMISOLE;

EID: 84863624104     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301243f     Document Type: Article

References (36)

1. For a review of azlactone chemistry, see: Fisk, J. S.; Mosey, R. A.; Tepe, J. J. Chem. Soc. Rev. 2007, 36, 1432
2. For a recent review of dynamic kinetic resolution, see: Pellissier, H. Tetrahedron 2011, 67, 3769
3. Crich, J. Z.; Brieva, R.; Marquart, P.; Gu, R. L.; Flemming, S.; Sih, C. J. J. Org. Chem. 1993, 58, 3252
4. Brown, S. A.; Parker, M.-C.; Turner, N. J. Tetrahedron: Asymmetry 2000, 11, 1687 and references cited therein
5. Seebach, D.; Jaeschke, G.; Gottwald, K.; Mastsuda, K.; Formisano, R.; Chaplin, D. A.; Breuning, M.; Bringmann, G. Tetrahedron 1997, 53, 7539
6. Liang, J.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1998, 63, 3154
7. Xie, L.; Hua, W.; Chan, A. S. C.; Leung, Y.-C. Tetrahedron: Asymmetry 1999, 10, 4715
8. Berkessel, A.; Cleemann, F.; Mukherjee, S.; Muller, T. N.; Lex, J. Angew. Chem., Int. Ed. 2005, 44, 807
9. Peschiulli, A.; Quigley, C.; Tallon, S.; Gun'ko, Y. K.; Connon, S. J. J. Org. Chem. 2008, 73, 6409
10. Yang, X.; Lu, G.; Birman, V. B. Org. Lett. 2010, 12, 892
11. Lu, G.; Birman, V. B. Org. Lett. 2011, 13, 356
12. Shiina, I.; Nakata, K.; Onda, Y. Eur. J. Org. Chem. 2008, 5887
13. Shiina, I.; Nakata, K.; Ono, K.; Onda, Y.; Itagaki, M. J. Am. Chem. Soc. 2010, 132, 11629
14. Yang, X.; Birman, V. B. Adv. Synth. Catal. 2009, 351, 2301
15. Yang, X.; Birman, V. B. Angew. Chem., Int. Ed. 2011, 50, 553
16. Yang, X.; Birman, V. B. Chem.-Eur. J. 2011, 17, 11296
17. Yang, X.; Liu, P.; Houk, K. N.; Birman, V. B., submitted.
18. Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351
19. Frisch, M. J Gaussian 09, revision B.01: Gaussian, Inc.: Wallingford, CT, 2010.
20. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
21. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
22. Thanthiriwatte, K. S.; Hohenstein, E. G.; Burns, L. A.; Sherrill, C. D. J. Chem. Theory Comput. 2010, 7, 88
23. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104
24. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378
25. For a review, see: Minkin, V. I.; Minyaev, R. M. Chem. Rev. 2001, 101, 1247
26. For examples of intramolecular nonbonded S-O interactions in structurally similar cases, see: Nagao, Y.; Hirata, T.; Goto, S.; Sano, S.; Kakehi, A.; Iizuka, K.; Shiro, M. J. Am. Chem. Soc. 1998, 120, 3104
27. Li, X.; Liu, P.; Houk, K. N.; Birman, V. B. J. Am. Chem. Soc. 2008, 130, 13836
28. Allen, F. H.; Baalham, C. A.; Lommerse, J. P. M.; Raithby, P. R. Acta Crystallogr., Sect. B 1998, 54, 320
29. Fischer, F. R.; Wood, P. A.; Allen, F. H.; Diederich, F. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 17290
30. Choudhary, A.; Gandla, D.; Krow, G. R.; Raines, R. T. J. Am. Chem. Soc. 2009, 131, 7244
31. Pal, T. K.; Sankararamakrishnan, R. J. Phys. Chem. B 2010, 114, 1038
32. Wu, Y. D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018
33. Paddonrow, M. N.; Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10638
34. Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199
35. Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61
36. Anh, N. T. Top. Curr. Chem. 1980, 88, 145