Structural studies of {6Li} 2-lithiopyrrolidines using NMR spectroscopy

Tetrahedron

Volumn 61, Issue 13, 2005, Pages 3271-3280

  Gawley, Robert E ^a,b   Klein, Rosalyn ^a,b   Ashweek, Neil J ^c   Coldham, Iain ^c,d  

^a UNIVERSITY OF ARKANSAS   (United States)

^b University of Miami   (United States)

^c UNIVERSITY OF EXETER   (United Kingdom)

^d UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

Lithiation; Lithiopyrrolidine; NMR spectroscopy; Organolithium; Tin lithium exchange

Indexed keywords

CARBONYL DERIVATIVE; ORGANOLITHIUM COMPOUND; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; SOLVATION; STRUCTURE ANALYSIS;

EID: 14844295032     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.098     Document Type: Article

References (48)

1. J. Clayden Organolithiums: Selectivity for Synthesis Vol. 23 2002 Pergamon Oxford
2. D.M. Hodgson Organolithiums in Enantioselective Synthesis Vol. 5 2003 Springer Heidelberg
3. Z. Rappoport I. Marek The Chemistry of Organolithium Compounds 2004 Wiley New York
4. R.E. Gawley, and I. Coldham Z. Rappoport I. Marek The Chemistry of Organolithium Compounds (Patai Series) 2004 997 1053
5. S.T. Kerrick, and P. Beak J. Am. Chem. Soc. 113 1991 9708 9710
6. N.A. Nikolic, and P. Beak Organic Syntheses, Coll Vol. 9 1998 Wiley New York 391 396 pp. 391-396
7. R.E. Gawley, and Q. Zhang J. Am. Chem. Soc. 115 1993 7515 7516
8. R.E. Gawley, and Q. Zhang J. Org. Chem. 60 1995 5763 5769
9. R.E. Gawley, and S. Campagna H. Rzepa J. Snyder ECHET96. Electronic Conference on Heterocyclic Chemistry 1996 Royal Society of Chemistry London
10. P. Beak, S.T. Kerrick, S. Wu, and J. Chu J. Am. Chem. Soc. 116 1994 3231 3239
11. R.K. Dieter, J.W. Dieter, C.W. Alexander, and N.S. Bhinderwala J. Org. Chem. 61 1996 2930 2931
12. R.K. Dieter, and S. Li J. Org. Chem. 62 1997 7726 7735
13. R.K. Dieter, K. Lu, and S.E. Velu J. Org. Chem. 65 2000 8715 8724
14. R.K. Dieter, C.W. Alexander, and L.E. Nice Tetrahedron 56 2000 2767 2778
15. R.K. Dieter, C.M. Topping, and L.E. Nice J. Am. Chem. Soc. 66 2001 2302 2311
16. R.K. Dieter, C.M. Topping, K.R. Chandupatla, and K. Lu J. Org. Chem. 123 2001 5132 5133
17. R.K. Dieter, G. Oba, K.R. Chandupatla, C.M. Topping, K. Lu, and R.T. Watson J. Org. Chem. 69 2004 3076 3086
18. R.K. Dieter, R.T. Watson, and R. Goswami Org. Lett. 6 2004 253 256
19. R.E. Gawley, Q. Zhang, and S. Campagna J. Am. Chem. Soc. 117 1995 11817 11818
20. I. Coldham, R. Hufton, and D.J. Snowden J. Am. Chem. Soc. 118 1996 5322 5323
21. I. Coldham, J. Fernandéz, K.N. Price, and D.J. Snowden J. Org. Chem. 65 2000 3788 3795
22. I. Coldham, and G.P. Vennall Chem. Commun. 2000 1569 1570
23. I. Coldham, R. Hufton, K.N. Price, R.E. Rathmell, D.G. Snowden, and G.P. Vennall Synthesis 2001 1523 1531
24. N.J. Ashweek, I. Coldham, D.J. Snowden, and G.P. Vennall Chem. Eur. J. 8 2002 195 207
25. I. Coldham, S. Dufour, T.F.N. Haxell, S. Howard, and G.P. Vennall Angew. Chem., Int. Ed. 41 2002 3887 3889
26. I. Coldham, S. Dufour, T.F.N. Haxell, and G.P. Vennall Tetrahedron 61 2005 this issue, doi:10.1016/j.tet.2005.01.096
27. E. Low, and R.E. Gawley J. Am. Chem. Soc. 122 2000 9562 9563
28. N.J. Ashweek, P. Brandt, I. Coldham, S. Dufour, R.E. Gawley, F. Hæffner, R. Klein, and G. Sanchez-Jimenez J. Am. Chem. Soc. 127 2005 449 457
29. J. Arnold, V. Knapp, J.A.R. Schmidt, and A. Shafir J. Chem. Soc., Dalton Trans. 2002 3273 3274
30. G. Boche, M. Marsch, J. Harbach, K. Harms, B. Ledig, F. Schubert, J.C.W. Lohrenz, and H. Ahlbrecht Chem. Ber. 126 1993 1887 1894
31. H.J. Reich, W.S. Goldenberg, B.Ö. Gudmundsson, A. W. Sanders, K.J. Kulicke, K. Simon, and I.A. Guzei J. Am. Chem. Soc. 123 2001 8067 8079
32. H.J. Reich, W.S. Goldenberg, A.W. Sanders, K.L. Jantzi, and C.T. Tzschucke J. Am. Chem. Soc. 125 2003 3509 3521
33. H. Ahlbrecht, J. Harbach, R.W. Hoffmann, and T. Ruhland Liebigs Ann. 1995 211 216
34. C. Gaul, P.I. Arvidsson, W. Bauer, R.E. Gawley, and D. Seebach Chem. Eur. J. 7 2001 4117 4125
35. Y. Ahn, G.I. Cardenas, J. Yang, and D. Romo Org. Lett. 3 2001 751 754
36. I. Coldham, R.C.B. Copley, T.F.N. Haxell, and S. Howard Org. Lett. 3 2001 3799 3801
37. G.R. Krow, S.B. Herzon, G. Lin, F. Qiu, and P.E. Sonnet Org. Lett. 2002 4
38. D. Iula, and R.E. Gawley J. Org. Chem. 65 2000 6196 6201
39. S. Raucher, and G.A. Koolpe J. Org. Chem. 43 1978 3794 3796
40. R.E. Gawley, E.J. Termine, and J. Aubé Tetrahedron Lett. 21 1980 3115 3118
41. W.H. Pearson, and E.P. Stevens J. Org. Chem. 63 1998 9812 9827
42. R.E. Gawley, and Q. Zhang Tetrahedron 50 1994 6077 6088
43. K.M. Bertini Gross, and P. Beak J. Am. Chem. Soc. 123 2001 315 321
44. W. Bauer P.v.R. Schleyer A.-M. Sapse Lithium Chemistry: A Theoretical and Experimental Overview 1995 Wiley New York 125 172
45. W. Bauer, W.R. Winchester, and P.v.R. Schleyer Organometallics 6 1987 2371 2379
46. G. Fraenkel, A. Chow, and W.R. Winchester J. Am. Chem. Soc. 112 1990 6190 6198
47. M.F. Lappert, L.M. Engelhardt, C.L. Raston, and A.H. White J. Chem. Soc. Chem., Commun. 1982 1323 1324
48. G. Hilmersson, and O. Davidsson J. Organomet. Chem. 489 1995 175 179