Nickel-catalysed asymmetric SN2′ substitution chemistry of Baylis-Hillman derived allylic electrophiles

Comptes Rendus Chimie

Volumn 10, Issue 3, 2007, Pages 206-212

  Novak, Andrew ^a   Fryatt, Ross ^a   Woodward, Simon ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Allylic substitution; Ferrophites; Monodentate phosphates; Organoaluminium

Indexed keywords

EID: 33947723939     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2006.10.008     Document Type: Article

References (35)

1. Reviews of Pd-catalysed allylation:
2. Trost B.M., and Van Vranken D.L. Chem. Rev. 96 (1996) 395
3. Braun M., and Meier T. Synlett 5 (2006) 661
4. Helmchen G., Kudis S., Sennhenn P., and Steinhagen H. Pure Appl. Chem. 69 (1997) 513
5. Helmchen G., and Pfaltz A. Acc. Chem. Res. 33 (2000) 336
6. Nobuyoshi N., and RajanBabu T.V. Tetrahedron Lett. 38 (1997) 1713
7. Chung K.-G., Miyake Y., and Uemura S. J. Chem. Soc., Perkin Trans. 1 16 (2000) 2725
8. Chung K.-G., Miyake Y., and Uemura S. J. Chem. Soc., Perkin Trans. 1 16 (2000) 15
9. Consiglio G., and Indolese A. Organometallics 10 (1991) 3425
10. Hiyama T., and Wakasa N. Tetrahedron Lett. 26 (1985) 3259
11. Hiyama T., Konishi M., Yokota K., and Kumada M. J. Organomet. Chem. 285 (1985) 359
12. Evidence for motif B: (g). Kurasawa H., Ohnishi H., Emoto M., Naoto K., Yoshikane M., and Shinji I.I. Organometallics 9 (1990) 3038
13. Wada M., and Wakabayashi T. J. Organomet. Chem. 96 (1975) 301
14. Selected examples of stabilised nucleophiles with Pd-catalysed systems:
15. von Matt P., Lloyd-Jones G.C., Minidis A.B.E., Pfaltz A., Macko L., Neuburger M., Zehnder M., Ru{combining double acute accent}egger H., and Pregosin P.S. Helv. Chim. Acta 78 (1995) 265
16. Boele M.D.K., Kamer P.C.J., Lutz M., Spek A.L., de Vries J.G., van Leeuwen P.W.N.M., and van Stijdonck G.P.F. Chem. Eur. J. 10 (2004) 6232
17. Hilgraf R., and Pfaltz A. Adv. Synth. Catal. 347 (2005) 61
18. Pfaltz A., and Lautens M. In: Jacobsen E.N., Pflatz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis vol. 2 (1999), Springer, New York 833
19. Ir-catalysed systems: (e). Polet D., Alexakis A., Tissot-Croset K., Corminboeuf C., and Ditrich K. Chem. Eur. J. 12 (2006) 3596
20. Lipowsky G., Miller N., and Helmchen G. Angew. Chem., Int. Ed. 43 (2004) 4595
21. Ru-catalysed systems: (g). Bruneau C., Renard J.-L., and Demerseman B. Chem. Eur. J. 12 (2006) 5178
22. W-catalysed systems: (h). Lehmann J., and Lloyd-Jones G.C. Tetrahedron 51 (1995) 8863
23. Mo-catalysed systems: (i). Malkov A., Baxendale I.R., Mansfield D., and Kočovskỳ P. J. Chem. Soc., Perkin Trans. 1 (2001) 1234
24. Albrow V.E., Blake A.J., Fryatt R., Wilson C., and Woodward S. Eur. J. Org. Chem. (2006) 2549
25. Riant O., Argouarch G., Guillaneux D., Samuel O., and Kagan H.B. J. Org. Chem. 63 (1998) 3511
26. For the specific compound see:. Pedersen H.L., and Johannsen M. J. Org. Chem. 67 (2002) 7982
27. Biswas K., Börner C., Gimeno J., Goldsmith P.J., Ramazzotti D., So A.L.K., and Woodward S. Tetrahedron 61 (2005) 1433
28. Goldsmith P.J., and Woodward S. Angew. Chem., Int. Ed. Engl. 44 (2005) 2235
29. Biswas K., Prieto O., Goldsmith P.J., and Woodward S. Angew. Chem., Int. Ed. Engl. 44 (2005) 2232
30. Biswas K., Chapron A., Cooper T., Fraser P.K., Novak A., Prieto O., and Woodward S. Pure Appl. Chem. 78 (2006) 511
31. Cooper T., Novak A., Walker M.D., Humphreys L.D., and Woodward S. Adv. Synth. Catal. 348 (2006) 686
32. Novak A., Walker M.D., Humphreys L.D., and Woodward S. Tetrahedron Lett. 47 (2006) 5767
33. Basavaiah D., Muthukumaran K., and Sreenivasulu B. Synthesis (2000) 545
34. Buggle K., Philbin E.M., and Ryan N.D. J. Chem. Soc., Perkin Trans. 1 (1972) 2630
35. Dauben W.G., Lodder G., and Robbins J.D. Nouv. J. Chim. 3 (1977) 243