Models for the basis of enantioselection in palladium mediated C-H activation reactions

Tetrahedron Asymmetry

Volumn 21, Issue 23, 2010, Pages 2782-2787

  Günay, M Emin ^a   Ilyashenko, Gennadiy ^a   Richards, Christopher J ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 78651410981     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.10.014     Document Type: Article

References (40)

1. Selected reviews: K. Godula, and D. Sames Science 312 2006 67 72
2. R.G. Bergman Nature 446 2007 391 393
3. I.V. Seregin, and V. Gevorgyan Chem. Soc. Rev. 36 2007 1173 1193
4. L.-C. Campeau, D.R. Stuart, and K. Fagnou Aldrichim. Acta 40 2007 35 41
5. B.-J. Li, S.-D. Yang, and Z.-J. Shi Synlett 2008 949 957
6. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
7. X. Chen, K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem. Int. Ed. 48 2009 5094 5115
8. O. Daugulis, H.-Q. Do, and D. Shabashov Acc. Chem. Res. 42 2009 1074 1086
9. (a) T.W. Lyons, and M.S. Sanford Chem. Rev. 110 2010 1147 1169
10. A.C. Cope, and R.W. Siekman J. Am. Chem. Soc. 87 1965 3272 3273
11. A.C. Cope, and E.C. Friedrich J. Am. Chem. Soc. 90 1968 909 913
12. J. Dupont, M. Pfeffer, and J. Spencer Eur. J. Inorg. Chem. 2001 1917 1927
13. J. Dupont, C.S. Consorti, and J. Spencer Chem. Rev. 105 2005 2527 2571
14. C.J. Richards L.-X. Dai, X.-L. Hou, Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications 2010 Wiley-VCH Weinheim 337 368
15. C.J. Richards, and H. Nomura Chem. Asian J. 5 2010 1726 1740
16. V.V. Dunina, E.D. Razmyslova, O.N. Gorunova, M.V. Livantsov, and Y.K. Grishin Tetrahedron: Asymmetry 14 2003 2331 2333
17. A.M. Stevens, and C.J. Richards Organometallics 18 1999 1346 1348
18. R.S. Prasad, C.E. Anderson, C.J. Richards, and L.E. Overman Organometallics 24 2005 77 81
19. F.X. Roca, M. Motevalli, and C.J. Richards J. Am. Chem. Soc. 127 2005 2388 2389
20. 9 For these examples this points to weakly mismatched and matched pairings, respectively.
21. A.D. Ryabov, I.K. Sakodinskaya, and A.K. Yatsimirsky J. Chem. Soc., Dalton Trans. 1985 2629 2638
22. D.L. Davies, S.M.A. Donald, and S.A. Macgregor J. Am. Chem. Soc. 127 2005 13754 13755
23. D. Garcia-Cuadrado, A.A.C. Braga, F. Maseras, and A.M. Echavarren J. Am. Chem. Soc. 128 2006 1066 1067
24. M. Lafrance, C.N. Rowley, T.K. Woo, and K. Fagnou J. Am. Chem. Soc. 128 2006 8754 8756
25. D. Garcia-Cuadrado, P. de Mendoza, A.A.C. Braga, F. Maseras, and A.M. Echavarren J. Am. Chem. Soc. 129 2007 6880 6886
26. S.I. Gorelsky, D. Lapointe, and K. Fagnou J. Am. Chem. Soc. 130 2008 10848 10849
27. L.-C. Campeau, M. Parisien, M. Leblanc, and K. Fagnou J. Am. Chem. Soc. 126 2004 9186 9187
28. E.J. Hennessy, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 12084 12085
29. T. Izumi, H. Watabe, and A. Kasahara Bull. Chem. Soc. Jpn. 54 1981 1711 1714
30. I.P. Smoliakova, K.J. Keuseman, D.C. Haagenson, D.M. Wellmann, P.B. Colligan, N.A. Kataeva, A.V. Churakov, L.G. Kuz'mina, and V.V. Dunina J. Organomet. Chem. 603 2000 86 97
31. M.E. Günay, and C.J. Richards Organometallics 28 2009 5833 5836
32. V.I. Sokolov, L.L. Troitskaya, and O.A. Reutov J. Organomet. Chem. 182 1979 537 546
33. B.M. Pettitt, and M. Karplus J. Phys. Chem. 92 1988 3994 3997
34. D.J. Tobias, and C.L. Brooks III J. Phys. Chem. 96 1992 3864 3870
35. R. Navarro, J. García, E.P. Urriolabeitia, C. Cativiela, and M.D. Diaz-de-Villegas J. Organomet. Chem. 490 1995 35 43
36. B.-F. Shi, N. Maugel, Y.-H. Zhang, and J.-Q. Yu Angew. Chem. Int. Ed. 47 2008 4882 4886
37. See also: R. Giri, B.-F. Shi, K.M. Engle, N. Maugel, and J.-Q. Yu Chem. Soc. Rev. 38 2009 3242 3272
38. B.-F. Shi, Y.-H. Zhang, J.K. Lam, D.-H. Wang, and J.-Q. Yu J. Am. Chem. Soc. 132 2010 460 461
39. H.M. Peng, L.-X. Dai, and S.-L. You Angew. Chem. Int. Ed. 49 2010 5826 5828
40. 2: A.K. Thakur, Ashish, and R. Kishore Chem. Commun. 1999 1643 1644