Enantioselective catalytic transannular ketone-ene reactions

Organic Letters

Volumn 15, Issue 16, 2013, Pages 4238-4241

  Rajapaksa, Naomi S ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; CHROMIUM; CYCLODECANE DERIVATIVE; KETONE; MESYLIC ACID DERIVATIVE; SCHIFF BASE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALCOHOLS; ALKENES; CATALYSIS; CHROMIUM; CYCLODECANES; KETONES; MESYLATES; SCHIFF BASES; STEREOISOMERISM;

EID: 84882754659     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401968m     Document Type: Article

References (47)

1. Marsault, E.; Toró, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243
2. Clarke, P. A.; Reeder, A. T.; Winn, J. Synthesis 2009, 5, 691
3. Balskus, E. P.; Jacobsen, E. N. Science 2007, 317, 1736
4. Chandler, C. L.; List, B. J. Am. Chem. Soc. 2008, 130, 6737
5. Jaschinski, T.; Hiersemann, M. Org. Lett. 2012, 14, 4114
6. Hodgson, D. M.; Lee, G. P.; Marriott, R. E.; Thompson, A. J.; Wisedale, R.; Witheringon J. Chem. Soc., Perkin Trans. 1 1998, 2151
7. Hodgson, D. M.; Robinson, L. A. Chem. Commun. 1999, 309
8. Inoue, M.; Sato, T.; Hirama, M. Angew. Chem., Int. Ed. 2006, 45, 4848
9. Inoue, M.; Lee, N.; Kasuya, S.; Sato, T.; Hirama, M. J. Org. Chem. 2007, 72, 3065
10. Knopff, O.; Kuhne, J.; Fehr, C. Angew. Chem., Int. Ed. 2007, 46, 1307
11. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021
12. Mikami, K.; Terada, M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; p 1143.
13. Clarke, M. L.; France, M. B. Tetrahedron 2008, 64, 9003
14. Clarke, M. L.; Jones, C. E. S.; France, M. B. Beilstein J. Org. Chem. 2007, 3, 24
15. Rueping, M.; Thiessmann, T.; Kuenkel, A.; Koenigs, R. M. Angew. Chem., Int. Ed. 2008, 47, 6798
16. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936
17. Yang, D.; Yang, M.; Zhu, N.-Y. Org. Lett. 2003, 5, 3749
18. Mikami, K.; Aikawa, K.; Kainuma, S.; Kawakami, Y.; Saito, T.; Sayo, N.; Kumobayashi, H. Tetrahedron: Asymmetry 2004, 15, 3885
19. Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W. J. Org. Chem. 2006, 71, 9751
20. Mikami, K.; Kawakami, Y.; Akiyama, K.; Aikawa, K. J. Am. Chem. Soc. 2007, 129, 12950
21. Zhao, J.-F.; Tsui, H.-Y.; Wu, P.-J.; Lu, J.; Loh, T.-P. J. Am. Chem. Soc. 2008, 130, 16492
22. Luo, H.-K.; Woo, Y.-L.; Schumann, H.; Jacob, C.; van Meurs, M.; Yang, H.-Y.; Tan, Y.-T. Adv. Synth. Catal. 2010, 352, 1356
23. Zheng, K.; Yang, Y.; Zhao, J.; Yin, C.; Lin, L.; Liu, X.; Feng, X. Chem.-Eur. J. 2010, 16, 9969
24. Zhao, Y.-J.; Li, B.; Tan, L.-J. S.; Shen, Z.-L.; Loh, T.-P. J. Am. Chem. Soc. 2010, 132, 10242
25. For a recent review of natural sesquiterpenoids, see: Fraga, B. M. Nat. Prod. Rep. 2011, 28, 1580
26. Nakazaki, M.; Yamamoto, K.; Naemura, K. Stereochemistry of Twisted Double Bond Systems. Topics in Current Chemistry, Vol. 125; Vogtle, F.; Weber, E., Eds.; Springer: Berlin, 1984; p 1.
27. Sauer, E. L. O.; Hooper, J.; Woo, T.; Barriault, L. J. Am. Chem. Soc. 2007, 129, 2112
28. Sauer, E. L. O.; Barriault, L. J. Am. Chem. Soc. 2004, 126, 8670
29. Divinyl alcohol 3 has been prepared by Barriault and coworkers. The route shown in Scheme 1 is a modified version of the one reported: Warrington, J. M.; Yap, G. P. A.; Barriault, L. Org. Lett. 2000, 2, 663
30. Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 4765
31. Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398
32. Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059
33. Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882
34. Joly, G. D.; Jacobsen, E. N. Org. Lett. 2002, 4, 1795
35. Ruck, R. T.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2003, 42, 4771
36. Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5, 2563
37. Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 6043
38. Grachan, M. L.; Tudge, M. T.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, 1469
39. Chavez, D. E.; Jacobsen, E. N. Org. Synth. 2005, 82, 34
40. Cope, A. C.; Banholzer, K.; Keller, H.; Pawson, B. A.; Whang, J. J.; Winkler, H. J. S. J. Am. Chem. Soc. 1965, 87, 3644
41. Westen, H. H. Helv. Chim. Acta 1964, 47, 575
42. Binsch, G.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 5158
43. Tomooka, K.; Ezawa, T.; Inoue, H.; Uehara, K.; Igawa, K. J. Am. Chem. Soc. 2011, 133, 1754
44. Reference 13.
45. Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron Lett. 1983, 24, 1157
46. Chair-like transition structures that are consistent with reaction outcomes have been determined computationally for diastereoselective thermal ketone-ene reactions of (E)-cyclodecenones: Terada, Y.; Yamamura, S. Tetrahedron Lett. 1979, 20, 1623
47. A kinetic resolution of planar chiral cyclic ethers has been achieved through an enantioselective transannular [2,3]-Wittig rearrangement: Tomooka, K.; Komine, N.; Fujiki, D.; Nakai, T.; Yanagitsuru, S. J. Am. Chem. Soc. 2005, 127, 12182