Organic base catalyzed carbonyl allylation of methyl trifluoropyruvate with activated alkenes

Tetrahedron

Volumn 65, Issue 1, 2009, Pages 83-86

  Zhang, Fan ^a   Wang, Xiao Jin ^a   Cai, Chen Xin ^a   Liu, Jin Tao ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Activated alkene; Allylation; Homoallylic alcohol; Methyl trifluoropyruvate; Organic base

Indexed keywords

ALCOHOL; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC ACID; HYDROXYL GROUP; METHYL TRIFLUOROPYRUVATE; PYRUVIC ACID DERIVATIVE; QUININE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; FLUORINE NUCLEAR MAGNETIC RESONANCE; ISOMERIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; X RAY DIFFRACTION;

EID: 56949107216     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.002     Document Type: Article

References (53)

1. Banks R.E., Smart B.E., and Tatlow J.C. Organofluorine Chemistry: Principle and Commercial Applications (1994), Plenum, New York, NY
2. Hiyama T. Organofluorine Compounds: Chemistry and Application (2000), Springer, Berlin
3. Filler R., Kobayashi Y., and Yagupolskii L.M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (1993), Elsevier, Amsterdam
4. Ojima I., McCarthy J.R., and Welch J.T. Biomedical Frontiers of Fluorine Chemistry (1996), American Chemical Society, Washington, DC
5. Soloshonok V.A. Fluorine-Containing Synthons (2005), American Chemical Society, Washington, DC
6. For recent review, see:
7. Marek I., and Sklute G. Chem. Commun. (2007) 1683-1691
8. Hall D.G. Synlett (2007) 1644-1655
9. Denmak S.E., and Fu J. Chem. Rev. 103 (2003) 2763-2793
10. For respective examples, see:
11. Ren H., Dunet G., Mayer P., and Knochel P. J. Am. Chem. Soc. 129 (2007) 5376-5377
12. Marek I., and Sklute G. J. Am. Chem. Soc. 128 (2006) 4642-4649
13. Kennedy J.W.J., and Hall D.G. Angew. Chem., Int. Ed. 42 (2003) 4732-4739
14. Ishiyama T., Ahiko T., and Miyaura N. J. Am. Chem. Soc. 124 (2002) 12414-12415
15. Waltz K.M., Gavenonis J., and Walsh P.J. Angew. Chem., Int. Ed. 41 (2002) 3697-3699
16. For recent examples, see:
17. Kim I.S., Ngai M.Y., and Krische M.J. J. Am. Chem. Soc. 130 (2008) 6340-6341
18. Shibahara F., Bower J.F., and Krische M.J. J. Am. Chem. Soc. 130 (2008) 6338-6339
19. Bower J.F., Skucas E., Patman R.L., and Krische M.J. J. Am. Chem. Soc. 129 (2007) 15134-15135
20. Miller J.J., and Sigman M.S. J. Am. Chem. Soc. 129 (2007) 2752-2753, and references therein
21. Yuan Y., Zhang X., and Ding K. Angew. Chem., Int. Ed. 42 (2003) 5478-5480
22. Okachi T., Fujimoto K., and Onaka M. Org. Lett. 4 (2002) 1667-1669
23. Koh J.H., Larsen A.O., and Gagné M.R. Org. Lett. 3 (2001) 1233-1236
24. Evans D.A., Tregay S.W., Burgey C.S., Paras N.A., and Vojkovsky T. J. Am. Chem. Soc. 122 (2000) 7936-7943
25. Johnson J.S., and Evans D.A. Acc. Chem. Res. 33 (2000) 325-335
26. Mikami K., and Shimizu M. Chem. Rev. 92 (1992) 1021-1050
27. Xue J.W., Chen W., Li R., Zeng M., Du W., Yue L., Chen Y.-C., Wu Y., Zhu J., and Deng J.-G. Angew. Chem., Int. Ed. 46 (2007) 389-392
28. Liu T.-Y., Cui H.L., Long J., Li B.-J., Wu Y., Ding L.-S., and Chen Y.-C. J. Am. Chem. Soc. 129 (2007) 1878-1879
29. Bell M., Frisch K., and Jørgensen K.A. J. Org. Chem. 71 (2006) 5407-5410
30. Xie J.-W., Yue L., Xue D., Ma X.-L., Chen Y.-C., Wu Y., Zhu J., and Deng J.-G. Chem. Commun. (2006) 1563-1565
31. Poulsen T.B., Bell M., and Jørgensen K.A. Org. Biomol. Chem. 4 (2006) 63-70
32. Xue D., Chen Y.-C., Wang Q.-W., Cun L.-F., Zhu J., and Deng J.-G. Org. Lett. 7 (2005) 5293-5296
33. Poulsen T.B., Alemparte C., and Jørgensen K.A. J. Am. Chem. Soc. 127 (2005) 11614-11615
34. For recent papers using trifluoropyruvate as building blocks, see:
35. Ogawa S., Shibata N., Inagaki J., Nakamura S., Toru T., and Shiro M. Angew. Chem., Int. Ed. 46 (2007) 8666-8669
36. Shibata N., Fujimoto H., Mizuta S., Ogawa S., Ishiuchi Y., Nakamura S., and Toru T. Synlett (2006) 3484-3488
37. Deb I., Dadwal M., Mobin S.M., and Namboothiri I.N.N. Org. Lett. 8 (2006) 1201-1204
38. Zhao J.-L., Liu L., Sui Y., Liu Y.-L., Wang D., and Chen Y.-J. Org. Lett. 8 (2006) 6127-6130
39. Chaume G., Severen M.-C.V., Marinkovic S., and Brigaud T. Org. Lett. 8 (2006) 6123-6126
40. Skarpos H., Vorob'eva D.V., Osipov S.N., Odinets I.L., Breuer E., and Roeschenthaler G.-V. Org. Biomol. Chem. 4 (2006) 3669-3674
41. Abid M., and Torok B. Adv. Synth. Catal. 347 (2005) 1797-1803
42. Takikawa G., Katagiri T., and Uneyama K. J. Org. Chem. 70 (2005) 8811-8816
43. Sibgatulin D.A., Volochnyuk D.M., and Kostyuk A.N. Synlett (2005) 1907-1911
44. Toeroek B., Abid M., London G., Esquibel J., Toeroek M., Mhadgut S.C., Yan P., and Prakash G.K.S. Angew. Chem., Int. Ed. 44 (2005) 3086-3089
45. Lyle M.P.A., Draper N.D., and Wilson P.D. Org. Lett. 7 (2005) 901-904
46. Hall Jr. H.K. J. Am. Chem. Soc. 79 (1957) 5441-5444, and references therein
47. Faltin C., Fleming E.M., and Connon S.J. J. Org. Chem. 69 (2004) 6496-6499, and references therein
48. Braude E.A., and Nachod F.C. Determination of Organic Structures by Physical Methods (1955), Academic, New York, NY
49. Streitwieser A., and Kim Y.-J. J. Am. Chem. Soc. 122 (2000) 11783-11786, and references therein
50. 2=0.1685. Crystallographic data for the structures of 2a reported in this paper have been deposited with the Cambridge Crystallographic Data Centre (CCDC 689148). Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, United Kingdom (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.uk).
51. Popp F.D., and Catala A. J. Org. Chem. 26 (1960) 2738-2740
52. Verhé R., Kimpe N., Courtheyn D., Buyck L., and Schamp N. Tetrahedron 38 (1982) 3649-3660
53. Cardillo G., Fabbroni S., Gentilucci L., Ginaotti M., and Tolomelli A. Synth. Commun. 33 (2003) 1587-1594