Enantioselective copper catalysed 1,4-conjugate addition reactions using chiral N-heterocyclic carbenes

Journal of Organometallic Chemistry

Volumn 690, Issue 24-25, 2005, Pages 5672-5695

  Winn, Caroline L ^a   Guillen, Frédéric ^b   Pytkowicz, Julien ^c   Roland, Sylvain ^c   Mangeney, Pierre ^c   Alexakis, Alexandre ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF GENEVA   (Switzerland)

^c SORBONNE UNIVERSITÉ   (France)

Author keywords

Chiral N heterocyclic carbenes; Conjugate addition; Copper catalysed; Enantioselective; Imidazolinium salts; Silver(I)

Indexed keywords

COPPER; SILVER; STABILITY; SYNTHESIS (CHEMICAL); ZINC;

CHIRAL N-HETEROCYCLIC CARBENES; CONJUGATE ADDITION; COPPER CATALYZED; ENANTIOSELECTIVE; IMIDAZOLINIUM SALTS;

CATALYSIS;

EID: 27744557334     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.07.024     Document Type: Article

References (53)

1. D.J. Cardin, B. Cetinkaya, P. Dixneuf, and M.F. Lappert Chem. Rev. 72 1972 545 574
2. W.A. Herrmann, C.-P. Reisinger, and M. Spiegler J. Organomet. Chem. 557 1998 93 96
3. V. Caló, A. Nacci, L. Lopez, and N. Mannarini Tetrahedron Lett. 41 2000 8973 8976
4. H.M. Lee, and S.P. Nolan Org. Lett. 2 2000 2053 2055
5. J.P. Morgan, and R.H. Grubbs Org. Lett. 2 2000 3153 3155
6. C. Zhang, J. Huang, M.L. Trundell, and S.P. Nolan J. Org. Chem. 64 1999 3804 3805
7. V. Caló, R. Del Sole, A. Nacci, E. Schingaro, and F. Scordari Eur. J. Org. Chem. 2000 869 871
8. W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1291 1309
9. T.J. Seiders, D.W. Ward, and R.H. Grubbs Org. Lett. 3 2001 3255 3288
10. M.T. Powell, D.-R. Hou, M.C. Perry, X. Cui, and K. Burgess J. Am. Chem. Soc. 123 2001 8878 8879
11. P.K. Fraser, and S. Woodward Tetrahedron Lett. 42 2001 2747 2749
12. F. Guillen, C.L. Winn, and A. Alexakis Tetrahedron Asymmetry 12 2001 2083 2086
13. A. Alexakis, C.L. Winn, F. Guillen, J. Pytkowicz, S. Roland, and P. Mangeney Adv. Synth. Catal. 345 2003 345 348
14. J. Pytkowicz, S. Roland, and P. Mangeney Tetrahedron Asymmetry 12 2001 2086 2088
15. H. Clavier, L. Coutable, J.-C. Guillemin, and M. Mauduit Tetrahedron Asymmetry 16 2005 921 924
16. P.L. Arnold, M. Rodden, K.M. Davis, A.C. Scarisbrick, A.J. Blake, and C. Wilson Chem. Commun. 2004 1612 1613
17. S. Tominiga, Y. Oi, T. Kato, D.K. An, and S. Okamoto Tetrahedron Lett. 45 2004 5585 5588
18. A.O. Larsen, W. Leu, C.N. Oberhuber, J.E. Campbell, and A.H. Hoveyda J. Am. Chem. Soc. 126 2004 11130 11131
19. A. Alexakis, J. Vastra, and P. Mangeney Tetrahedron Lett. 38 1997 7745 7748
20. A.J. Arduengo III, R.L. Harlow, and M.A. Kline J. Am. Chem. Soc. 113 1991 361 363
21. N. Krause, and A. Hoffmann-Roder Synthesis 2001 171 196
22. A. Alexakis, and C. Benhaim Eur. J. Org. Chem. 2002 3221 3236
23. K. Bambridge, M.J. Begley, and N.S. Simpkins Tetrahedron Lett. 35 1994 3391 3394
24. G. Martelli, S. Mori, and D. Savoia Tetrahedron 56 2000 8367 8374
25. S. Saba, A.-M. Brescia, and M.K. Kaloustain Tetrahedron Lett. 32 1991 5031 5034
26. P. Mangeney, A. Alexakis, F. Grojean, and J.F. Normant Tetrahedron Lett. 29 1988 2675 2676
27. M. Periasamy, G. Srinivas, G.V. Karunkar, and P. Bharathi Tetrahedron Lett. 40 1999 7577 7580
28. R. Hulst, N. Koen de Vries, and B.L. Feringa Tetrahedron Asymmetry 5 1994 699 708
29. S. Lee, and J.F. Hartwig J. Org. Chem. 66 2001 3402 3415
30. A.J. Arduengo III, H.V.R. Dias, R.L. Harlow, and M.A. Kline J. Am. Chem. Soc. 114 1992 5530 5534
31. A.J. Arduengo III, J.R. Goerlich, and W.J. Marshall J. Am. Chem. Soc. 117 1995 11027 11028
32. A. Alexakis, J. Burton, J. Vastra, C. Benhaim, X. Fournioux, A. van den Heuvel, J.M. Levêque, and F. Mazé Eur. J. Org. Chem. 2000 4011 4027
33. A. Alexakis, C. Benhaim, S. Rosset, and M. Humam J. Am. Chem. Soc. 124 2002 5262 5263
34. G.D. Allred, and L. Liebeskind J. Am. Chem. Soc. 118 1996 2748 2749
35. We had previously observed that changing the counteranion to a halide led to a decrease in enantiomeric excess and in this case, the iodocomponds gave less that 3% ee.
36. F.M. Rivas, U. Riaz, A. Giessert, J.A. Smulik, and S.T. Diver Org. Lett. 3 2001 2673 2676
37. F.M. Rivas, U. Riaz, and S.T. Diver Tetrahedron Asymmetry 11 2000 1703 1707
38. W.A. Herrmann, L.J. Goossen, C. Koecher, and G.R. Artus J. Angew. Chem. Int. Ed. 35 1996 2805 2807
39. W.A. Herrmann, M. Elison, J. Fischer, C. Kocher, and G.R. Artus J. Chem. Eur. J. 2 1996 777 780
40. D. Seebach, A.K. Beck, and A. Heckel Angew. Chem. Int. Ed. 40 2001 92 138
41. D. Seebach, R. Dahinden, R.E. Martin, A.K. Beck, D.A. Plattner, and F.N.M. Kühnle J. Org. Chem. 60 1995 1788 1799
42. D. Seebach, D.A. Plattner, A.K. Beck, Y.M. Wang, D. Hunziker, and W. Petter Helv. Chim. Acta 75 1992 2171 2209
43. A.J. Arduengo III, H.W.R. Dias, J.C. Calabrese, and F. Davidson Organometallics 12 1993 3405 3409
44. H.M.J. Wang, and I.J.B. Lin Organometallics 17 1998 972 975
45. J. Pytkowicz, S. Roland, and P. Mangeney J. Organomet. Chem. 631 2001 157 163
46. D.S. McGuiness, and K.J. Cavell Organometallics 19 2000 741 748
47. S. Roland, P. Mangeney, and A. Alexakis Synthesis 1999 228 230
48. A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, and P. Mangeney J. Chem. Soc., Perkin Trans. 1 2001 949 951
49. H.T. Dieck, and J. Dietrich Chem. Ber. 117 1984 649 701
50. A. Alexakis, and C. Benhaim Org. Lett. 2 2000 2579 2581
51. G. Domany, A. Gere, M. Paroczai, C. Szantay, and G. Ferenczy Pharmazie 48 1993 941 942
52. 13C NMR spectrum with high enough resolution, nor to measure its optical rotation. Moreover, elemental analysis of 62 performed on the same sample gave irreproducible results.
53. W.L.F. Armarengo, and D.D. Perrin Purification of Laboratory Chemicals fourth ed. 1998 Butterworth and Heinemann Bath