Enantioselective synthesis of β-trifluoromethyl-βlactones via NHC-catalyzed ketene - ketone cycloaddition reactions

Organic Letters

Volumn 11, Issue 18, 2009, Pages 4029-4031

  Wang, Xiao Na ^a   Shao, Pan Lin ^a   Lv, Hui ^a   Ye, Song ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; DRUG DERIVATIVE; ETHYLENE DERIVATIVE; KETENE; KETONE; KETONE BODY; LACTONE; METHANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; ETHYLENES; KETONE BODIES; KETONES; LACTONES; METHANE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 70349103398     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901290z     Document Type: Article

References (59)

1. (a) Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, 2004.
2. (b) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993.
3. (a) Asymmetric Fluoroorganic Chemistry; Ramachandran, P. V., Ed.; ACS Symposium Series; American Chemical Society: Washington, DC, 2000.
4. (b) Abid, M.; Torok, B. Adv. Synth. Catal. 2005, 347, 1797.
5. (a) Ma, J. A.; Cahard, D. Chem. Rev. 2004, 104, 6119.
6. (b) Uneyama, K.; Katagiri, T.; Amii, H. Acc. Chem. Res. 2008, 41, 817.
7. (a) Fernández, R.; Martín-Zamora, E.; Pareja, C.; Vázquez, J.; Díez, E.; Monge, A.; Lassaletta, J. M., Angew. Chem., Int. Ed. 1998, 37, 3428.
8. (b) Motoki, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2007, 9, 2997.
9. (c) Martina, S. L. X.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Chem. Commun. 2006, 4093.
10. (d) Bøgevig, A.; Gothelf, K. V.; Jørgensen, K. A. Chem. - Eur. J. 2002, 8, 5652.
11. (e) Bandini, M.; Sinisi, R.; Umani-Ronchi, A. Chem. Commun. 2008, 4360.
12. (f) Rueping, M.; Theissmann, T.; Kuenkel, A.; Koenigs, R. M. Angew. Chem., Int. Ed. 2008, 47, 6798.
13. (g) Zhao, J.-L.; Liu, L.; Gu, C.-L.; Wang, D.; Chen, Y.-J. Tetrahedron Lett. 2008, 49, 1476.
14. (h) Shi, M.; Liu, X.-G.; Guo, Y.-W.; Zhang, W. Tetrahedron 2007, 63, 12731.
15. (i) Tur, F.; Saá, J. M. Org. Lett. 2007, 9, 5079.
16. (j) Motoki, R.; Tomita, D.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 8083.
17. For the highlights and reviews, see: (a) Schneider, C. Angew. Chem., Int. Ed. 2002, 41, 744.
18. (b) Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403.
19. (c) Wang, Y.; Tennyson, R. L.; Romo, D. Heterocycles 2004, 64, 605.
20. For the enantioselective synthesis of β-lactones via [2 + 2] cycloaddition of ketenes and aldehydes, see: (a) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166.
21. (b) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742.
22. (c) Cortez, G. S.; Tennyson, R. L.; Romo, D. J. Am. Chem. Soc. 2001, 123, 7945.
23. (d) Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125.
24. (e) Calter, M. A.; Tretyak, O. A.; Flaschenriem, C. Org. Lett. 2005, 7, 1809.
25. (f) Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2004, 43, 6358.
26. (g) Gnandesikan, V.; Corey, E. J. Org. Lett. 2006, 8, 4943.
27. (h) Linn, W. J. U.S. Patent 3,271,419, Sept. 6, 1966.
28. (i) For reviews of NHC-catalyzed reactions, see: (a) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
29. (b) Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
30. (c) Zeitler, K. Angew. Chem., Int. Ed. 2005, 44, 7506.
31. (d) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
32. (a) Sheehan, J.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666.
33. (b) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217.
34. (c) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696.
35. (d) Li, G.-Q.; Dai, L.-X.; You, S.-L. Chem. Commun. 2007, 852.
36. (d) Stetter, H. Angew. Chem., Int. Ed. 1976, 15, 639.
37. (e) Enders, D.; Han, J.; Henseler, A. Chem. Commun. 2008, 3989.
38. (a) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205.
39. (b) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
40. (c) Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905.
41. (d) Fischer, C.; Smith, S. W.; Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 1472.
42. (e) He, L.; Jian, T.-Y.; Ye, S. J. Org. Chem. 2007, 72, 7466.
43. (a) Song, J. J.; Tan, Z.; Reeves, J. T.; Gallou, F.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2005, 7, 2193.
44. (b) Wu, J.; Sun, X.; Ye, S.; Sun, W. Tetrahedron Lett. 2006, 47, 4813.
45. (a) Hirano, K.; Piel, I.; Glorius, F. Adv. Synth. Catal. 2008, 350, 984.
46. (b) Li, Y.; Zhao, Z.-A.; He, H.; You, S.-L. Adv. Synth. Catal. 2008, 350, 1885.
47. (c) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205.
48. (d) Burstein, C.; Tschan, S.; Xie, X.; Glorius, F. Synthesis 2006, 2418.
49. (a) Zhang, Y.-R.; He, L.; Wu, X.; Shao, P.-L.; Ye, S. Org. Lett. 2008, 10, 277.
50. (b) Duguet, N.; Campbell, C. D.; Slawin, A. M. Z.; Smith, A. D. Org. Biomol. Chem. 2008, 6, 1108.
51. (c) He, L.; Lv, H.; Zhang, Y.-R.; Ye, S. Org. Chem. 2008, 73, 8101.
52. (d) Zhang, Y.-R.; Lv, H.; Zhou, D.; Ye, S. Chem. - Eur. J. 2008, 14, 8473.
53. (e) Huang, X.-L.; He, L.; Shao, P.-L.; Ye, S. Angew. Chem., Int. Ed. 2009, 48, 192.
54. (f) For convenience, the corresponding NHCs prepared from the precursors 4a-h were denoted as NHCs 4a'-h'.
55. 3.
56. (h) Lv, H.; Zhang, Y.-R.; Huang, X.-L.; Ye, S. Adv. Synth. Catal. 2008, 350, 2715.
57. (i) He, L.; Zhang, Y.-R.; Huang, X.-L.; Ye, S. Synthesis 2008, 2825.
58. (j) The different stereochemical outcome of bulky ketenes is also observed in the [4 + 2] cycloaddition reaction of ketenes with Nbenzoyldiazenes (ref 16e).
59. 4 led to a complex instead of the corresponding diol. See Supporting Information for details.