Catalytic conjugate addition of acyl anion equivalents promoted by fluorodesilylation

Organic Letters

Volumn 16, Issue 1, 2014, Pages 70-73

  Denmark, Scott E ^a   Cullen, Lindsey R ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84891757019     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403041k     Document Type: Article

References (39)

1. Seebach, D. Angew. Chem., Int. Ed. 1979, 18, 239
2. Lever, O. W., Jr. Tetrahedron 1976, 32, 1943
3. Yus, M.; Nájera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147
4. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606
5. Piancatelli, G.; D'Auria, M.; D'Onofrio, F. Synthesis 1994, 867
6. Graening, T.; Thrun, F. Furans and their Benzo Derivatives: Synthesis. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Amsterdam, 2008; Vol. 3, pp 497-569.
7. Bergman, J.; Janosik, T. Five-Membered Heterocycles: Pyrrole and Related Systems. In Modern Heterocyclic Chemistry; Alvarez-Builla, J.; Vaquero, J. J.; Barluenga, J., Eds.; Wiley-VCH: Weinheim, 2011; Vol. 4, pp 269-275.
8. Willis, M. C. Chem. Rev. 2010, 110, 725
9. Lueng, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202
10. Srikanth, G. S. C.; Castle, S. L. Tetrahedron 2005, 61, 10377
11. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991
12. Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. 1965, 4, 1077
13. For a review, see: Albright, J. D. Tetrahedron 1983, 39, 3207
14. Brown, C. A.; Yamaichi, A. J. Chem. Soc., Chem. Commun. 1979, 100
15. Mukaiyama, T.; Narasaka, K.; Furusato, M. J. Am. Chem. Soc. 1972, 94, 8641
16. Ager, D. J.; East, M. B. J. Org. Chem. 1986, 51, 3983
17. Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407
18. de Alaniz, J. R.; Rovis, T. Synlett 2009, 8, 1189
19. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
20. Phillips, E. M.; Chan, A.; Scheidt, K. A. Aldrichimica Acta 2009, 42, 55
21. DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 10872
22. Gawronski, J.; Wascinska, N.; Gajewy, J. Chem. Rev. 2008, 108, 5227
23. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560
24. Ooi, T.; Maruoka, K. Acc. Chem. Res. 2004, 37, 526
25. Hosomi, A.; Shirahata, A.; Sakurai, H. Tetrahedron Lett. 1978, 19, 3043
26. Bohsako, A.; Asakura, C.; Shioiri, T. Synlett 1995, 1033
27. Mizuta, S.; Shibata, N.; Akiti, S.; Fujimoto, H.; Nakamura, S.; Toru, T. Org. Lett. 2007, 9, 3707
28. Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273
29. Grotjahn, D. B.; Andersen, N. H. J. Chem. Soc., Chem. Commun. 1981, 306
30. Andersen, N. H.; McCrae, D. A.; Grotjahn, D. B.; Gabhe, S. Y.; Theodore, L. J.; Ippolito, R. M.; Sarkar, T. K. Tetrahedron 1981, 37, 4069
31. Michida, M.; Mukaiyama, T. Chem.-Asian J. 2008, 3, 1592
32. Wadhwa, K.; Verkade, J. G. Tetrahedron Lett. 2009, 50, 4307
33. Capperucci, A.; Cerè, V.; Degl'Innocenti, A.; Nocentini, T.; Pollicino, S. Synlett 2002, 1447
34. Carlson, R. M.; Helquist, P. M. J. Org. Chem. 1968, 33, 2596
35. Gokel, G. W.; Gerdes, H. M.; Dishong, D. M. J. Org. Chem. 1980, 45, 3634
36. Biddle, M. M.; Reich, H. J. J. Org. Chem. 2006, 71, 4031
37. Abatjoglou, A. G.; Eliel, E. L.; Kuyper, L. F. J. Am. Chem. Soc. 1977, 99, 8262
38. Juaristi, E.; Cruz-Sánchez, J. S.; Ramos-Morales, F. R. J. Org. Chem. 1984, 49, 4912
39. Reich, H. J.; Borst, J. P.; Dykstra, R. R. Tetrahedron 1994, 50, 5869