Salen promoted enantioselective nazarov cyclizations of activated and unactivated dienones

Journal of the American Chemical Society

Volumn 135, Issue 13, 2013, Pages 4988-4991

  Hutson, Gerri E ^a   Türkmen, Yunus E ^a   Rawal, Viresh H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL CENTERS; CYCLIZATIONS; DIENONES; ENANTIOSELECTIVE; NAZAROV CYCLIZATION; NAZAROV REACTION;

ENANTIOSELECTIVITY; METAL COMPLEXES;

CYCLIZATION;

CYCLOPENTENE DERIVATIVE; CYCLOPENTENOID; DIENONE; ETHYLENEDIAMINE; PHENOL DERIVATIVE; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; COVALENT BOND; CRYSTAL STRUCTURE; CYCLIZATION; ENANTIOSELECTIVITY; NAZAROV CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; CHROMIUM; COORDINATION COMPLEXES; CYCLIZATION; ETHYLENEDIAMINES; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84875789275     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja401908m     Document Type: Article

References (44)

1. Habermas, K. L.; Denmark, S. E. Org. React. 1994, 45, 1
2. Harmata, M. Chemtracts 2004, 416
3. Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577
4. Pellissier, H. Tetrahedron 2005, 61, 6479
5. Tius, M. A. Eur. J. Org. Chem. 2005, 2193
6. Nakanishi, W.; West, F. G. Curr. Opin. Drug Discovery Dev. 2009, 12, 732
7. Liang, G.; Xu, Y.; Seiple, I. B.; Trauner, D. J. Am. Chem. Soc. 2006, 128, 11022
8. Berger, G. O.; Tius, M. A. J. Org. Chem. 2007, 72, 6473
9. He, W.; Huang, J.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2008, 130, 300
10. Gao, S.; Wang, Q.; Chen, C. J. Am. Chem. Soc. 2009, 131, 1410
11. Malona, J. A.; Cariou, K.; Frontier, A. J. J. Am. Chem. Soc. 2009, 131, 7560
12. Vaidya, T.; Eisenberg, R.; Frontier, A. J. ChemCatChem 2011, 3, 1531
13. Shimada, N.; Stewart, C.; Tius, M. A. Tetrahedron 2011, 67, 5851
14. Aggarwal, V. K.; Belfield, A. J. Org. Lett. 2003, 5, 5075
15. Contemporaneously, Trauner reported one example of an enantioselective Nazarov cyclization (53% yield, 61% ee): Liang, G.; Gradl, N.; Trauner, D. Org. Lett. 2003, 5, 4931
16. Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544
17. Nie, J.; Zhu, H. W.; Cui, H.; Hua, M.; Ma, J. Org. Lett. 2007, 9, 3053
18. Walz, I.; Togni, A. Chem. Commun. 2008, 4315
19. Yaji, K.; Shindo, M. Synlett 2009, 2524
20. Kawatsura, M.; Kajita, K.; Hayase, S.; Itoh, T. Synlett 2010, 1243
21. Cao, P.; Deng, C.; Zhou, Y.; Sun, X.; Zheng, J.; Xie, Z.; Tang, Y. Angew. Chem., Int. Ed. 2010, 49, 4463
22. Rueping, M.; Ieawsuwan, W.; Antonchick, A. P.; Nachtsheim, B. J. Angew. Chem., Int. Ed. 2007, 46, 2097
23. Rueping, M.; Ieawsuwan, W. Adv. Synth. Cat. 2009, 351, 78
24. Bow, W. F.; Basak, A. K.; Jolit, A.; Vicic, D. A.; Tius, M. A. Org. Lett. 2010, 12, 440
25. Basak, A. K.; Shimada, N.; Bow, W. F.; Vicic, D. A.; Tius, M. A. J. Am. Chem. Soc. 2010, 132, 8266
26. Rueping, M.; Ieawsuwan, W. Chem. Commun. 2011, 11450
27. Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 7843
28. Huang, Y.; Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163
29. Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950
30. Takenaka, N.; Huang, Y.; Rawal, V. H. Tetrahedron 2002, 58, 8299
31. McGilvra, J. D.; Rawal, V. H. Synlett 2004, 2440
32. Early precedent: Schaus, S. E.; BraÌŠnalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403
33. Hutson, G. E.; Davé, A. H.; Rawal, V. H. Org. Lett. 2007, 9, 3869
34. Achard, T. R. J.; Clutterbuck, L. A.; North, M. Synlett 2005, 1828
35. McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563
36. Cozzi, P. G. Chem. Rev. 2004, 104, 410
37. Larrow, J. F.; Jacobsen, E. N. Top. Organomet. Chem. 2004, 6, 123
38. Katsuki, T. Coord. Chem. Rev. 1995, 140, 189
39. Togni, A.; Venazani, L. M. Angew. Chem., Int. Ed. 1994, 33, 497
40. Chiral vanadium (IV) salen complex was reported to provide no enantioselectivity in the Nazarov reaction: Walz, I.; Bertogg, A.; Togni, A. Eur. J. Org. Chem. 2007, 2680
41. Reed, C. A. Chem. Commun. 2005, 1669
42. Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292
43. Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 10521
44. Enantioselective cyclization of acyclic α-alkoxy dienones was recently reported: Raja, S.; Ieawsuwan, W.; Korotkov, V.; Rueping, M. Chem. Asian J. 2012, 7, 2361