Metal-mediated asymmetric alkylation using chiral N-heterocyclic carbenes derived from chiral amines

Coordination Chemistry Reviews

Volumn 251, Issue 5-6, 2007, Pages 702-717

  Douthwaite, Richard E ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Alkylation; Catalysis; Chirality; Copper; N Heterocyclic carbenes; Palladium

Indexed keywords

EID: 33846838592     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2006.08.003     Document Type: Review

References (52)

1. Arduengo A.J., Harlow R.L., and Kline M. J. Am. Chem. Soc. 113 (1991) 361
2. Bourissou D., Guerret O., Gabbai F.P., and Bertrand G. Chem. Rev. 100 (2000) 39
3. Herrmann W.A. Angew. Chem. Int. Ed. 41 (2002) 1291
4. Crabtree R.H. J. Organomet. Chem. 690 (2005) 5451
5. Abernethy C.D., Codd G.M., Spicer M.D., and Taylor M.K. J. Am. Chem. Soc. 125 (2003) 1128
6. Perry M.C., and Burgess K. Tetrahedron: Asymmetry 14 (2003) 951
7. Cesar V., Bellemin-Laponnaz S., and Gade L.H. Chem. Soc. Rev. 33 (2004) 619
8. Coleman A.W., Hitchcock P.B., Lappert M.F., Maskell R.K., and Muller J.H. J. Organomet. Chem. 296 (1985) 173
9. Coleman A.W., Hitchcock P.B., Lappert M.F., Maskell R.K., and Muller J.H. J. Organomet. Chem. 250 (1983) C9
10. Reetz M.T., Sell T., Meiswinkel A., and Mehler G. Angew. Chem. Int. Ed. 42 (2003) 790
11. van den Berg M., Minnaard A.J., Schudde E.P., van Esch J., de Vries A.H.M., de Vries J.G., and Feringa B.L. J. Am. Chem. Soc. 122 (2000) 11539
12. Clyne D.S., Jin J., Gallucci J.C., and RajanBabu T.V. Org. Lett. 2 (2000) 1125
13. Perry M.C., Cui X.H., Powell M.T., Hou D.R., Reibenspies J.H., and Burgess K. J. Am. Chem. Soc. 125 (2003) 113
14. Gade L.H., Cesar V., and Bellemin-Laponnaz S. Angew. Chem. Int. Ed. 43 (2004) 1014
15. Lee S., and Hartwig J.F. J. Org. Chem. 66 (2001) 3402
16. Ma Y.D., Song C., Ma C.Q., Sun Z.J., Chai Q., and Andrus M.B. Angew. Chem. Int. Ed. 42 (2003) 5871
17. Seiders T.J., Ward D.W., and Grubbs R.H. Org. Lett. 3 (2001) 3225
18. Duan W.L., Shi M., and Rong G.B. Chem. Commun. (2003) 2916
19. Bonnet L.G., Douthwaite R.E., and Hodgson R. Organometallics 22 (2003) 4384
20. Bonnet L.G., Douthwaite R.E., and Kariuki B.M. Organometallics 22 (2003) 4187
21. Douthwaite R.E., and Hodgson R. J. Organomet. Chem. 690 (2005) 5822
22. Bappert E., and Helmchen G. Synlett (2004) 1789
23. Becht J.M., Bappert E., and Helmchen G. Adv. Synth. Catal. 347 (2005) 1495
24. Van Veldhuizen J.J., Campbell J.E., Giudici R.E., and Hoveyda A.H. J. Am. Chem. Soc. 127 (2005) 6877
25. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921
26. Yorimitsu H., and Oshima K. Angew. Chem. Int. Ed. 44 (2005) 4435
27. Sato Y., Yoshino T., and Mori M. Org. Lett. 5 (2003) 31
28. Sato Y., Yoshino T., and Mori M. J. Organomet. Chem. 690 (2005) 5753
29. Bonnet L.G., Douthwaite R.E., Hodgson R., Houghton J., Kariuki B.M., and Simonovic S. Dalton Trans. (2004) 3528
30. Wang H.M.J., and Lin I.J.B. Organometallics 17 (1998) 972
31. Lewis A.K.D., Caddick S., Cloke F.G.N., Billingham N.C., Hitchcock P.B., and Leonard J. J. Am. Chem. Soc. 125 (2003) 10066
32. Grasa G.A., Viciu M.S., Huang J.K., and Nolan S.P. J. Org. Chem. 66 (2001) 7729
33. Junker J., Reif B., Steinhagen H., Junker B., Felli I.C., Reggelin M., and Griesinger C. Chem. Eur. J. 6 (2000) 3281
34. Steinhagen H., Reggelin M., and Helmchen G. Angew. Chem. Int. Ed. Engl. 36 (1997) 2108
35. Widhalm M., Nettekoven U., Kalchhauser H., Mereiter K., Calhorda M.J., and Felix V. Organometallics 21 (2002) 315
36. Helmchen G., and Pfaltz A. Acc. Chem. Res. 33 (2000) 336
37. Larsen A.O., Leu W., Oberhuber C.N., Campbell J.E., and Hoveyda A.H. J. Am. Chem. Soc. 126 (2004) 11130
38. Van Veldhuizen J.J., Garber S.B., Kingsbury J.S., and Hoveyda A.H. J. Am. Chem. Soc. 124 (2002) 4954
39. Tominaga S., Oi Y., Kato T., An D.K., and Okamoto S. Tetrahedron Lett. 45 (2004) 5585
40. Winn C.L., Guillen F., Pytkowicz J., Roland S., Mangeney P., and Alexakis A. J. Organomet. Chem. 690 (2005) 5672
41. Alexakis A., Winn C.L., Guillen F., Pytkowicz J., Roland S., and Mangeney P. Adv. Synth. Catal. 345 (2003) 345
42. Pytkowicz J., Roland S., and Mangeney P. Tetrahedron: Asymmetry 12 (2001) 2087
43. Guillen F., Winn C.L., and Alexakis A. Tetrahedron: Asymmetry 12 (2001) 2083
44. Arnold P.L., Rodden M., Davis K.M., Scarisbrick A.C., Blake A.J., and Wilson C. Chem. Commun. (2004) 1612
45. Clavier H., Coutable L., Guillemin J.C., and Mauduit M. Tetrahedron: Asymmetry 16 (2005) 921
46. Clavier H., Coutable L., Toupet L., Guillemin J.C., and Mauduit M. J. Organomet. Chem. 690 (2005) 5237
47. Woodward S. Chem. Soc. Rev. 29 (2000) 393
48. Nakamura E., and Mori S. Angew. Chem. Int. Ed. 39 (2000) 3751
49. Fraser P.K., and Woodward S. Tetrahedron Lett. 42 (2001) 2747
50. Stambuli J.P., Buhl M., and Hartwig J.F. J. Am. Chem. Soc. 124 (2002) 9346
51. A recent report describes the construction of all-carbon quaternary chiral centers via copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones using NHC-alkoxide ligands.
52. Martin D., Kehrli S., d'Augustin M., Clavier H., Mauduit M., and Alexakis A. J. Am. Chem. Soc. 128 (2006) 8416