QSAR analysis of the catalytic asymmetric ethylation of ketone using physical steric parameters of chiral ligand substituents

Tetrahedron

Volumn 70, Issue 6, 2014, Pages 1289-1297

  Huang, Huayin ^a   Zong, Hua ^a   Shen, Bin ^a   Yue, Huifeng ^a   Bian, Guangling ^a   Song, Ling ^a  

^a FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

Author keywords

Asymmetric catalysis; Ketones; Molar refraction; Sterimol parameters

Indexed keywords

ACETOPHENONE; ALCOHOL; DIETHYLZINC; KETONE; PHOSPHORAMIDIC ACID;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; PHYSICAL PARAMETERS; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 84892830723     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.12.054     Document Type: Article

References (66)

1. J.D. Oslob, B. Akermark, P. Helquist, and P.O. Norrby Organometallics 16 1997 3015 3021
2. K.B. Lipkowitz, C.A. D'Hue, T. Sakamoto, and J.N. Stack J. Am. Chem. Soc. 124 2002 14255 14267
3. K.B. Lipkowitz, and M.C. Kozlowski Synlett 2003 1547 1565
4. M.C. Kozlowski, and M. Panda J. Org. Chem. 68 2003 2061 2076
5. S. Alvarez, S. Schefzick, K. Lipkowitz, and D. Avnir Chem. - Eur. J. 9 2003 5832 5837
6. M.C. Kozlowski, S.L. Dixon, M. Panda, and G. Lauri J. Am. Chem. Soc. 125 2003 6614 6615
7. J.C. Ianni, V. Annamalai, P.W. Phuan, M. Panda, and M.C. Kozlowski Angew. Chem., Int. Ed. 45 2006 5502 5505
8. J. Chen, J.W. Wen, M.Z. Li, and Y.P. Tianpa J. Mol. Catal. A: Chem. 258 2006 191 197
9. M. Urbano-Cuadrado, J.J. Carbo, A.G. Maldonado, and C. Bo J. Chem. Inf. Model. 47 2007 2228 2234
10. K.N. Houk, and P.H.Y. Cheong Nature 455 2008 309 313
11. S.J. Zuend, and E.N. Jacobsen J. Am. Chem. Soc. 131 2009 15358 15374
12. P.J. Donoghue, P. Helquist, P.O. Norrby, and O. Wiest J. Am. Chem. Soc. 131 2009 410 411
13. A.G. Maldonado, and G. Rothenberg Chem. Soc. Rev. 39 2010 1891 1902
14. S.E. Denmark, N.D. Gould, and L.M. Wolf J. Org. Chem. 76 2011 4260 4336
15. S.E. Denmark, N.D. Gould, and L.M. Wolf J. Org. Chem. 76 2011 4337 4357
16. K.H. Jensen, and M.S. Sigman Angew. Chem., Int. Ed. 46 2007 4748 4750
17. J.J. Miller, and M.S. Sigman Angew. Chem., Int. Ed. 47 2008 771 774
18. M.S. Sigman, and J.J. Miller J. Org. Chem. 74 2009 7633 7643
19. K.H. Jensen, and M.S. Sigman J. Org. Chem. 75 2010 7194 7201
20. K.H. Jensen, J.D. Webb, and M.S. Sigman J. Am. Chem. Soc. 132 2010 17471 17482
21. K.C. Harper, and M.S. Sigman Proc. Natl. Acad. Sci. U.S.A. 108 2011 2179 2183
22. K.C. Harper, and M.S. Sigman Science 333 2011 1875 1878
23. J.L. Gustafson, M.S. Sigman, and S.J. Miller Org. Lett. 12 2010 2794 2797
24. K.C. Harper, E.N. Bess, and M.S. Sigman Nat. Chem. 4 2012 366 374
25. K.C. Harper, and M.S. Sigman J. Org. Chem. 78 2013 2813 2818
26. K.C. Harper, S.C. Vilardi, and M.S. Sigman J. Am. Chem. Soc. 135 2013 2482 2485
27. S.J. Miller Nat. Chem. 4 2012 344 345
28. J. Rudolph, C. Bolm, and P.O. Norrby J. Am. Chem. Soc. 127 2005 1548 1552
29. S. Sciabola, A. Alex, P.D. Higginson, J.C. Mitchelll, M.J. Snowden, and I. Morao J. Org. Chem. 70 2005 9025 9027
30. H.J. Zhu, J.X. Jiang, S. Saebo, and C.U. Pittman J. Org. Chem. 70 2005 261 267
31. J. Huang, J.C. Ianni, J.E. Antoline, R.P. Hsung, and M.C. Kozlowski Org. Lett. 8 2006 1565 1568
32. M.C. Kozlowski, and J.C. Ianni J. Mol. Catal. A: Chem. 324 2010 141 145
33. H.Y. Huang, H. Zong, G.L. Bian, and L. Song J. Org. Chem. 77 2012 10427 10434
34. K. Fuji Chem. Rev. 93 1993 2037 2066
35. E.J. Corey, and A. Guzman-Perez Angew. Chem., Int. Ed. 37 1998 388 401
36. L. Pu Tetrahedron 59 2003 9873 9886
37. D.J. Ramon, and M. Yus Angew. Chem., Int. Ed. 43 2004 284 287
38. D.J. Ramon, and M. Yus Tetrahedron Lett. 39 1998 1239 1242
39. D.J. Ramon, and M. Yus Tetrahedron 54 1998 5651 5666
40. C. Garcia, L.K. LaRochelle, and P.J. Walsh J. Am. Chem. Soc. 124 2002 10970 10971
41. M. Yus, D.J. Ramon, and O. Prieto Tetrahedron: Asymmetry 13 2002 2291 2293
42. M. Yus, D.J. Ramon, and O. Prieto Eur. J. Org. Chem. 2003 2745 2748
43. M. Yus, D.J. Ramon, and O. Prieto Tetrahedron: Asymmetry 14 2003 1103 1114
44. C.A. de Parrodi, and P.J. Walsh Synlett 2004 2417 2420
45. V.J. Forrat, D.J. Ramon, and M. Yus Tetrahedron: Asymmetry 16 2005 3341 3344
46. S.J. Jeon, H.M. Li, C. Garcia, L.K. LaRochelle, and P.J. Walsh J. Org. Chem. 70 2005 448 455
47. S.J. Jeon, H.M. Li, and P.J. Walsh J. Am. Chem. Soc. 127 2005 16416 16425
48. P.G. Cozzi Angew. Chem., Int. Ed. 45 2006 2951 2954
49. M. Hatano, T. Miyamoto, and K. Ishihara Org. Lett. 9 2007 4535 4538
50. M.A. Fernandez-lbanez, B. Macia, A.J. Minnaard, and B.L. Feringa Chem. Commun. 2008 2571 2573
51. V.J. Forrat, D.J. Ramon, and M. Yus Tetrahedron: Asymmetry 19 2008 537 541
52. M. Hanato, and K. Ishihara Chem. Rec. 8 2008 143 155
53. M. Hatano, T. Mizuno, and K. Ishihara Tetrahedron 67 2011 4417 4424
54. M. Hatano, R. Gouzu, T. Mizuno, H. Abe, T. Yamada, and K. Ishihara Catal. Sci. Technol. 1 2011 1149 1158
55. B. Shen, H.Y. Huang, G.L. Bian, H. Zong, and L. Song Chirality 25 2013 561 566
56. A. Verloop, and J. Tipker D. Hadzi, J.B. Borka, QSAR in Drug Design and Toxicology 1987 Elsevier Amsterdam 97 100
57. C. Hansch, and A. Leo Exploring QSAR: Fundamentals and Applications in Chemistry and Biology 1995 American Chemical Society Washington, DC
58. C. Hansch, A. Leo, and D. Hoekma Exploring QSAR: Hydrophobic, Electronic, and Steric Constants 1995 American Chemical Society Washington, DC
59. V. Consonni, and R. Todeschini Handbook of Molecular Descriptors 2000 Wiley-VCH Weinheim, Germany/New York, NY 297 298
60. H. Kubinyi QSAR: Hansch Analysis and Related Approaches 1993 Wiley-VCH Weinheim, Germany/New York, NY 40 43
61. M. Charton J. Am. Chem. Soc. 97 1975 1552 1556
62. M. Charton J. Org. Chem. 41 1976 2217 2220
63. R.W. Taft J. Am. Chem. Soc. 74 1952 2729 2732
64. R.W. Taft J. Am. Chem. Soc. 75 1953 4538 4539
65. M. Charton J. Org. Chem. 42 1977 3535 3538
66. A.V.R. Madduri, S.R. Harutyunyan, and A.J. Minnaard Angew. Chem., Int. Ed. 51 2012 3164 3167