Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed lactonization

Journal of the American Chemical Society

Volumn 134, Issue 14, 2012, Pages 6068-6071

  Dobish, Mark C ^a   Johnston, Jeffrey N ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST LOADINGS; COUNTERIONS; ENANTIOSELECTION; ENANTIOSELECTIVE; HIGH YIELD; LACTONIZATION; REAGENT SYSTEMS; UNSATURATED CARBOXYLIC ACIDS;

CARBOXYLIC ACIDS; ENANTIOSELECTIVITY; PROTONS;

CATALYSTS;

BRONSTED ACID; CARBOXYLIC ACID; COUNTERION; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; ELECTROPHILICITY; ENANTIOSELECTIVITY; HYDROGEN BOND; REACTION TIME;

CARBOXYLIC ACIDS; CATALYSIS; HALOGENS; HEXANES; HYDROGEN BONDING; IONS; LIGANDS; MODELS, CHEMICAL; STEREOISOMERISM; SUCCINIMIDES; TEMPERATURE;

EID: 84859621571     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja301858r     Document Type: Article

References (47)

1. Dowle, M. D.; Davies, D. I. Chem. Soc. Rev. 1979, 8, 171
2. Cui, X.-L.; Brown, R. S. J. Org. Chem. 2000, 65, 5653
3. Denmark, S. E.; Burk, M. T.; Hoover, A. J. J. Am. Chem. Soc. 2010, 132, 1232
4. Denmark, S. E.; Burk, M. T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20655
5. Chen, G.; Ma, S. Angew. Chem., Int. Ed. 2010, 49, 8306
6. Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Synlett 2011, 1335
7. Castellanos, A.; Fletcher, S. P. Chem.-Eur. J. 2011, 17, 5766
8. Grossman, R. B.; Trupp, R. J. Can. J. Chem. 1998, 76, 1233
9. Garnier, J. M.; Robin, S.; Rousseau, G. Eur. J. Org. Chem. 2007, 3281
10. Sakakura, A.; Ukai, A.; Ishihara, K. Nature 2007, 445, 900
11. Cai, Y.; Liu, X.; Hui, Y.; Jiang, J.; Wang, W.; Chen, W.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2010, 49, 6160
12. Zhang, Y.; Shibatomi, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 15038
13. Uyanik, M.; Yasui, T.; Ishihara, K. Bioorg. Med. Chem. Lett. 2009, 19, 3848
14. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474
15. Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Org. Lett. 2011, 13, 2738
16. Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2011, 133, 9164
17. Whitehead, D. C.; Yousefi, R.; Jaganathan, A.; Borhan, B. J. Am. Chem. Soc. 2010, 132, 3298
18. Yousefi, R.; Whitehead, D. C.; Mueller, J. M.; Staples, R. J.; Borhan, B. Org. Lett. 2011, 13, 608
19. Murai, K.; Matsushita, T.; Nakamura, A.; Fukushima, S.; Shimura, M.; Fujioka, H. Angew. Chem., Int. Ed. 2010, 49, 9174
20. Wang, M.; Gao, L. X.; Yue, W.; Mai, W. P. Synth. Commun. 2004, 34, 1023
21. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332
22. Jaganathan, A.; Garzan, A.; Whitehead, D. C.; Staples, R. J.; Borhan, B. Angew. Chem., Int. Ed. 2011, 50, 2593
23. Lozano, O.; Blessley, G.; Martinez del Campo, T.; Thompson, A. L.; Giuffredi, G. T.; Bettati, M.; Walker, M.; Borman, R.; Gouverneur, V. Angew. Chem., Int. Ed. 2011, 50, 8105
24. Li, H.; Zhang, F.-M.; Tu, Y.-Q.; Zhang, Q.-W.; Chen, Z.-M.; Chen, Z.-H.; Li, J. Chem. Sci. 2011, 2, 1839
25. Chen, Z.-M.; Zhang, Q.-W.; Chen, Z.-H.; Li, H.; Tu, Y.-Q.; Zhang, F.-M.; Tian, J.-M. J. Am. Chem. Soc. 2011, 133, 8818
26. Gustafson, J. L.; Lim, D.; Miller, S. J. Science 2010, 328, 1251
27. Sakakura, A.; Sakuma, M.; Ishihara, K. Org. Lett. 2011, 13, 3130
28. Hatano, M.; Sugiura, Y.; Akakura, M.; Ishihara, K. Synlett 2011, 1247
29. Hatano, M.; Maki, T.; Moriyama, K.; Arinobe, M.; Ishihara, K. J. Am. Chem. Soc. 2008, 130, 16858
30. Davis, T. A.; Dobish, M. C.; Schwieter, K. E.; Chun, A. C.; Johnston, J. N. Org. Synth. 2012, 89, 380
31. Shackleford, J. P.; Shen, B.; Johnston, J. N. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 44
32. Davis, T. A.; Johnston, J. N. Chem. Sci. 2011, 2, 1076
33. Dobish, M. C.; Johnston, J. N. Org. Lett. 2010, 12, 5744
34. Shen, B.; Makley, D. M.; Johnston, J. N. Nature 2010, 465, 1027
35. Davis, T. A.; Wilt, J. C.; Johnston, J. N. J. Am. Chem. Soc. 2010, 132, 2880
36. Shen, B.; Johnston, J. N. Org. Lett. 2008, 10, 4397
37. Wilt, J. C.; Pink, M.; Johnston, J. N. Chem. Commun. 2008, 4177
38. Singh, A.; Johnston, J. N. J. Am. Chem. Soc. 2008, 130, 5866
39. Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 3418
40. Singh, A.; Yoder, R. A.; Shen, B.; Johnston, J. N. J. Am. Chem. Soc. 2007, 129, 3466
41. Denmark, S. E.; Burk, M. T. Org. Lett. 2012, 14, 256
42. Hess, A. S.; Yoder, R. A.; Johnston, J. N. Synlett 2006, 147
43. Akiyama, T. Chem. Rev. 2007, 107, 5744
44. Christ, P.; Lindsay, A. G.; Vormittag, S. S.; Neudörfl, J.-M.; Berkessel, A.; O'Donoghue, A. C. Chem.-Eur. J. 2011, 17, 8524
45. Sigman, M. S.; Jensen, K. H. Angew. Chem., Int. Ed. 2007, 46, 4748
46. Kim, H.; Yen, C.; Preston, P.; Chin, J. Org. Lett. 2006, 8, 5239
47. Kim, H.; Soon, M. S.; Chin, J.; Kim, B. M. Aldrichimica Acta 2008, 41, 77