Unexpected effect of the fluorine atom on the optimal ligand-to-palladium ratio in the enantioselective Pd-catalyzed allylation reaction of fluorinated enol carbonates

Chemical Communications

Volumn , Issue 28, 2008, Pages 3251-3253

  Bélanger, Étienne ^a   Houzé, Clément ^a   Guimond, Nicolas ^a   Cantin, Katy ^a   Paquin, Jean François ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA FLUOROKETONE DERIVATIVE; CARBONIC ACID DERIVATIVE; FLUORINE; KETONE DERIVATIVE; LIGAND; PALLADIUM;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; ENANTIOSELECTIVITY; FLUORINATION; REACTION ANALYSIS;

EID: 47249151303     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b803097a     Document Type: Article

References (43)

1. T. Hiyama, in Organofluorine Compounds: Chemistry and Applications, ed., H. Yamamoto,, Springer-Verlag, Berlin, Heidelberg, New York, 2000, pp. 1-23 and pp. 137-182
2. A. M. Thayer Chem. Eng. News 2006 84 15
3. J.-A. Ma D. Cahard Chem. Rev. 2004 104 6119
4. C. Bobbio V. Gouverneur Org. Biomol. Chem. 2006 4 2065
5. K. L. J. Kirk J. Fluorine Chem. 2006 127 1013
6. J.-P. Bégué D. J. Bonnet-Delpon J. Fluorine Chem. 2006 127 992
7. S. Purser P. R. Moore S. Swallow V. Gouverneur Chem. Soc. Rev. 2008 37 320
8. M. Marhold A. Buer H. Hiemstra J. H. van Maarseveen G. Haufe Tetrahedron Lett. 2004 45 57
9. F. Grein A. C. Chen D. Edwards C. M. Crudden J. Org. Chem. 2006 71 861
10. S. Kobayashi H. Tanaka H. Amii K. Uneyama Tetrahedron 2003 59 1547
11. C. M. Crudden A. C. Chen L. A. Calhoun Angew. Chem., Int. Ed. 2000 39 2851
12. T. Ernet A. H. Maulitz E.-U. Würthwein G. J. Haufe J. Chem. Soc., Perkin Trans. 1 2001 1929
13. W. Heitz A. Knebelkamp Macromol. Rapid Commun. 1991 12 69
14. S. J. Getty W. T. J. Borden J. Am. Chem. Soc. 1991 113 4334
15. J. Banus H. J. Emeléus R. N. J. Haszeldine J. Chem. Soc. 1951 60
16. J.-F. Paquin and M. Lautens, in Comprehensive Asymmetric Catalysis: Supplement 2, ed., E. N. Jacobsen,,, A. Pfaltz, and, H. Yamamoto,, Springer-Verlag, Berlin, 2004, pp. 73-95
17. A. Pfaltz and M. Lautens, in Comprehensive Asymmetric Catalysis, ed., E. N. Jacobsen,,, A. Pfaltz,,, H. Yamamoto,, Springer, New York, 1999, vol. 2, pp. 833-884
18. B. M. J. Trost J. Org. Chem. 2004 69 5813
19. B. M. Trost and C. Lee, in Catalytic Asymmetric Synthesis, ed., I. Ojima,, Wiley-VCH, New York, 2nd edn, 2000, pp. 593-649
20. G. J. Helmchen J. Organomet. Chem. 1999 576 203
21. B. M. Trost Chem. Pharm. Bull. 2002 50 1
22. B. M. Trost D. L. Van Vranken Chem. Rev. 1996 96 395
23. B. M. Trost Acc. Chem. Res. 1996 29 355
24. M. Braun T. Meier Synlett 2006 661
25. I. Bélanger K. Cantin O. Messe M. Tremblay J.-F. Paquin J. Am. Chem. Soc. 2007 129 1034
26. D. C. Behenna B. M. Stoltz J. Am. Chem. Soc. 2004 126 15044
27. J. A. Keith D. C. Behenna J. T. Mohr S. Ma S. C. Marinescu J. Oxgaard B. M. Stoltz W. A. Goddard III J. Am. Chem. Soc. 2007 129 11876
28. V. A. Brunet D. O'Hagan Angew. Chem., Int. Ed. 2008 47 1179
29. G. K. S. Prakash P. Beier Angew. Chem., Int. Ed. 2006 45 2172
30. P. M. Pihko Angew. Chem., Int. Ed. 2006 45 544
31. G. Helmchen A. Pfaltz Acc. Chem. Res. 2000 33 336
32. J. M. Williams Synlett 1996 705
33. B. M. Trost J. Xu J. Am. Chem. Soc. 2005 127 2846
34. B. M. Trost J. Xu J. Am. Chem. Soc. 2005 127 17180
35. X. Cheng K. K. Hii Tetrahedron: Asymmetry 2003 14 2045
36. D.-R. Hou J. H. Reibenspies K. Burgess J. Org. Chem. 2001 66 206
37. A. M. Porte J. Reibenspies K. Burgess J. Am. Chem. Soc. 1998 120 9180
38. K. Burgess A. M. Porte Tetrahedron: Asymmetry 1998 9 2465
39. R. Rasappan M. Hager A. Gissibl O. Reiser Org. Lett. 2006 8 6099
40. G. C. Lloyd-Jones C. P. Butts Tetrahedron 1998 54 901
41. E. C. Burger B. R. Barron J. A. Tunge Synlett 2006 2854
42. J. T. Mohr D. C. Behenna A. M. Harned B. M. Stoltz Angew. Chem., Int. Ed. 2005 44 6924
43. M. Nakamura A. Hajra K. Endo E. Nakamura Angew. Chem., Int. Ed. 2005 44 7248