Diastereoselective synthesis of trifluoromethylated γ-butyrolactones via N-heterocyclic carbene-catalyzed conjugated umpolung of α,β- unsaturated aldehydes

Advanced Synthesis and Catalysis

Volumn 350, Issue 7-8, 2008, Pages 984-988

  Hirano, Keiichi ^a   Piel, Isabel ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

butyrolactones; N heterocyclic carbenes; Organocatalysis; Organofluorine compounds; Trifluoromethyl substitution; Umpolung

Indexed keywords

EID: 53849128873     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800051     Document Type: Article

References (64)

1. a) E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824;
2. Angew. Chem. Int. Ed. 2007, 46, 2768;
3. b) N-Heterocyclic Carbenes in Transition Metal Catalysis, (Ed.: F. Glorius), Springer, Heidleberg, Berlin, 2007;
4. c) N-Heterocyclic Carbenes in Synthesis, (Ed.: S. P. Nolan), Wiley-VCH, Weinheim, 2006;
5. d) F. E. Hahn, Angew. Chem. 2006, 118, 1374;
6. Angew. Chem. Int. Ed. 2006, 45, 1348;
7. e) K. J. Cavell, D. S. McGuinness, Coord. Chem. Rev. 2004, 248, 671;
8. f) E. Peris, R. H. Crabtree, Coord. Chem. Rev. 2004, 248, 2239;
9. g) W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1291;
10. h) O. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39;
11. i) A. J. Arduengo, III. Acc. Chem. Res. 1999, 32, 913.
12. For a comprehensive review on NHC-catalyzed reactions, see: a) D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606.
13. For further reviews, see: b) N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007, 119, 3046;
14. Angew. Chem. Int. Ed. 2007, 46, 2988;
15. c) D. Enders, T. Balensiefer, T. Acc. Chem. Res. 2004, 37, 534;
16. d) J. S. Johnson, Angew. Chem. 2004, 116, 1348;
17. Angew. Chem. Int. Ed. 2004, 43, 1326;
18. e) M. Christmann, Angew. Chem. 2005, 117, 2688;
19. Angew. Chem. Int. Ed. 2005, 44, 2632;
20. f) K. Zeitler, Angew. Chem. 2005, 117, 7674;
21. Angew. Chem. Int. Ed. 2005, 44, 7506.
22. C. Burstein, S. Tschan, X. Xie, F. Glorius, Synthesis 2006, 2418.
23. a) S. S. Sohn, E. L. Rosen, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 14370;
24. b) S. S. Sohn, J. W. Bode, Org. Lett. 2005, 7, 3873;
25. c) C. Burstein, F. Glorius, Angew. Chem. 2004, 116, 6331;
26. Angew. Chem. Int. Ed. 2004, 43, 6205;
27. d) W. Schrader, P. P. Handayani, C. Burstein, F. Glorius, Chem. Commun. 2007, 716;
28. e) X. Xie, S Tschan, F. Glorius, Magn. Reson. Chem. 2007, 45, 381;
29. f) V. Nair, S. Vellalath, M. Poonoth, R. Mohan, E. Suresh, Org. Lett. 2006, 8, 507.
30. M. He, J. W. Bode, J. Am. Chem. Soc. 2008; 130, 418.
31. M. He, J. W. Bode, Org. Lett. 2005, 7, 3131.
32. a) V. Nair, S. Vellalath, M. Poonoth, E. Suresh, J. Am. Chem. Soc. 2006, 128, 8736;
33. b) P.-C. Chiang, J. Kaeobamrung, J. W. Bode, J. Am. Chem. Soc. 2007, 129, 3520;
34. c) E. M. Phillips, M. Wadamoto, A. Chan, K. A. Scheidt, Angew. Chem. 2007, 119, 3167;
35. Angew. Chem. Int. Ed. 2007, 46, 3107.
36. For some related organocatalyzed reactions, see: a) K. Y.-K. Chow, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 8126;
37. b) N. T. Reynolds, J. Read deAlaniz, T. Rovis, J. Am. Chem. Soc. 2004, 126, 9518;
38. c) A. Chan, K. A. Scheidt, Org. Lett. 2005, 7, 905;
39. d) N. T. Reynolds, T. Rovis, J. Am. Chem. Soc. 2005, 127, 16406;
40. e) K. Zeitler, Org. Lett. 2006, 8, 637;
41. f) M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 8418;
42. g) C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 1472;
43. h) M. He, G. J. Uc, J. W. Bode, J. Am. Chem. Soc. 2006; 128, 15088;
44. i) J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798;
45. j) D. Enders, O. Niemeier, T. Balensiefer, Angew. Chem. 2006, 118, 1491;
46. Angew. Chem. Int. Ed. 2006, 45, 1463;
47. k) D. Enders, U. Kallfass, Angew. Chem. 2002, 114, 1822;
48. Angew. Chem. Int. Ed. 2002, 41, 1743;
49. l) Y. Hachisu, J. W. Bode, K. Suzuki, J. Am. Chem. Soc. 2003, 125, 8432;
50. see also: m) T. Dudding, K. N. Houk, Proc. Natl. Acad. Sci. USA 2004, 101, 5770.
51. A. Berkessel, J. A. Adrio, J. Am. Chem. Soc. 2006, 128, 13412, and references cited therein.
52. Modern synthesic methods for the synthesis of organofluorine compounds have been covered in two recent reviews: a) M. Shimizu, T. Hiyama, Angew. Chem. 2005, 117, 218;
53. Angew. Chem. Int. Ed. 2005, 44, 214;
54. b) J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119;
55. see also: c) special issue on "Fluorine in the Life Sciences", ChemBioChem. 2004, 5, 557-726;
56. d) P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004;
57. e) T. Hiyama, Organofluorine Compounds: Chemistry and Applications, Springer, Berlin, 2000.
58. [3].
59. a) R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719;
60. b) H. Stetter, Angew. Chem. 1976, 88, 695;
61. Angew. Chem. Int. Ed. Engl. 1976, 15, 639.
62. J. Pesch, K. Harms, T. Bach, Eur. J. Org. Chem. 2004, 2025.
63. The switch in the like/unlike selectivity in the case of 3j compared to the other products is due to a priority change of the substituents based on the CIP system.
64. Under these conditions, however, the reaction of cinnamaldehyde with 4-chlorobenzaldehyde as a less electrophilic carbonyl compound did not yield significant amounts of the corresponding lactone product.