Electronic effects of aryl-substituted bis(oxazoline) ligands on the outcome of asymmetric copper-catalysed C-H insertion and aromatic addition reactions

Tetrahedron Asymmetry

Volumn 24, Issue 20, 2013, Pages 1265-1275

  Slattery, Catherine N ^a   O'Keeffe, Sarah ^a   Maguire, Anita R ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; COPPER DERIVATIVE; LIGAND; OXAZOLINE DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 84886839102     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2013.09.009     Document Type: Article

References (35)

1. M. Doyle, M. McKervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides 1998 Wiley New York
2. R. Paulissen, H. Reimlinger, E. Hayez, A.J. Hubert, and P. Teyssié Tetrahedron Lett. 14 1973 2233 2236
3. R. Paulissen, A.J. Hubert, and P. Teyssie Tetrahedron Lett. 13 1972 1465 1466
4. R.G. Salomon, and J.K. Kochi J. Am. Chem. Soc. 95 1973 3300 3310
5. A. Nakamura, A. Konishi, Y. Tatsuno, and S. Otsuka J. Am. Chem. Soc. 100 1978 3443 3448
6. A. Nakamura, A. Konishi, R. Tsujitani, M. Kudo, and S. Otsuka J. Am. Chem. Soc. 100 1978 3449 3461
7. S. O'Keeffe, F. Harrington, and A.R. Maguire Synlett 2007 2367 2370
8. C.N. Slattery, L.-A. Clarke, S. O'Neill, A. Ring, A. Ford, and A.R. Maguire Synlett 2012 765 767
9. C.J. Flynn, C.J. Elcoate, S.E. Lawrence, and A.R. Maguire J. Am. Chem. Soc. 132 2010 1184 1185
10. C.N. Slattery, and A.R. Maguire Org. Biomol. Chem. 9 2011 667 669
11. C.N. Slattery, L.-A. Clarke, A. Ford, and A.R. Maguire Tetrahedron 69 2013 1297 1301
12. C.N. Slattery, A. Ford, and A.R. Maguire Tetrahedron 66 2010 6681 6705
13. G.i.C. Hargaden, and P.J. Guiry Chem. Rev. 109 2009 2505 2550
14. G. Desimoni, G. Faita, and K.A. Jorgensen Chem. Rev. 106 2006 3561 3651
15. G. Desimoni, G. Faita, and K.A. Jørgensen Chem. Rev. 111 2011 284 437
16. The targeted benzyl-substituted bis(oxazolines) 6, 7 and 8 are novel compounds. Thus, since no literature data was available to confirm the enantiopurity of the novel ligands, the synthesis of both enantiomers of 6, 7 and 8 and thus, the corresponding amino alcohols 11, 12 and 13, was undertaken to allow the determination of the enantiopurity of the final bis(oxazoline) ligands by chiral stationary phase HPLC analysis.
17. D.A. Evans, J.S. Johnson, and E.J. Olhava J. Am. Chem. Soc. 122 2000 1635 1649
18. V. Di Marzo, A. Ligresti, E. Morera, M. Nalli, and G. Ortar Bioorg. Med. Chem. 12 2004 5161 5169
19. J.P. Greenstein, and M. Winitz Chemistry of the Amino Acids 1961 John Wiley and Sons, Inc. New York
20. V. Caplar, Z. Raza, D. Katalenic, and M. Zinic Croat. Chem. Acta 76 2003 23 36
21. R. Devant, and M. Braun Chem. Ber. 119 1986 2191 2207
22. R.A. Kumar, G. Bhaskar, A. Madhan, and B. Venkateswara Rao Synth. Commun. 33 2003 2907 2916
23. D.A. Evans, G.S. Peterson, J.S. Johnson, D.M. Barnes, K.R. Campos, and K.A. Woerpel J. Org. Chem. 63 1998 4541 4544
24. A. Cornejo, J.M. Fraile, J.I. García, M.J. Gil, V. Martínez-Merino, J.A. Mayoral, E. Pires, and I. Villalba Synlett 2321 2005 2324
25. A.R. Maguire, L.L. Kelleher, and G. Ferguson J. Mol. Catal. B: Enzym. 1 1996 115 126
26. O.A. McNamara, and A.R. Maguire Tetrahedron 67 2011 9 40
27. K.-i. Kawasaki, and T. Katsuki Tetrahedron 53 1997 6337 6350
28. A.I. Meyers, D.R. Williams, G.W. Erickson, S. White, and M. Druelinger J. Am. Chem. Soc. 103 1981 3081 3087
29. P. Bravo, S. Capelli, M. Crucianelli, M. Guidetti, A.L. Markovsky, S.V. Meille, V.A. Soloshonok, A.E. Sorochinsky, F. Viani, and M. Zanda Tetrahedron 55 1999 3025 3040
30. J. Granander, R. Sott, and G. Hilmersson Tetrahedron 58 2002 4717 4725
31. E.S. Lazer, C.K. Miao, H.-C. Wong, R. Sorcek, D.M. Spero, A. Gilman, K. Pal, M. Behnke, and A.G. Graham J. Med. Chem. 37 1994 913 923
32. M.P. Bosch, F. Campos, I. Niubó, G. Rosell, J.L. Díaz, J. Brea, M.I. Loza, and A. Guerrero J. Med. Chem. 47 2004 4041 4053
33. Y. Combret, J. Duflos, G. Dupas, J. Bourguignon, and G. Quéguiner Tetrahedron: Asymmetry 4 1993 1635 1644
34. E.P. Kyba, J.M. Timko, L.J. Kaplan, F. De Jong, G.W. Gokel, and D.J. Cram J. Am. Chem. Soc. 100 1978 4555 4568
35. T.S. Cooper, P. Laurent, C.J. Moody, and A.K. Takle Org. Biomol. Chem. 2 2004 265 276