修正的一锅法Julia烯基化反应,将杂芳基砜和醛转变为相应的E-烯烃。砜的还原步在该反应中是不需要的。
反应机理
四唑的替代物
应用类似K+那样较大的配对离子和DME那样的极性溶剂有利于一个开放过渡态的形成(PT是苯基四唑)
反应实例
参考文献
1. (a) Baudin, J. B.; Hareau,G.; Julia, S. A.; Ruel, O. Tetrahedron Lett. 1991, 32,
1175-1178. (b) Baudin,J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Bull. Soc. Chim. Fr.
1993, 130, 336357.(c) Baudin, J. B.; Hareau, G.; Julia, S. A.; Loene, R.; Ruel, O.
Bull. Soc. Chim.Fr. 1993, 130, 856878. (d) Blakemore, P. R.; Cole, W. J.;
Kocienski, P. J.; Morely, A. Synlett1998, 2628.
2. Charette, A. B.; Lebel, H. J. Am. Chem.Soc. 1996, 118, 1032710328.
3. Blakemore, P. R.; Kocienski,P. J.; Morley, A.; Muir, K. J. Chem. Soc., Perkin Trans.
1 1999, 955968.
4. Williams, D. R.; Brooks, D.A.; Berliner, M. A. J. Am. Chem. Soc. 1999, 121,
49244925.
5. Kocienski, P. J.; Bell, A.;Blakemore, P. R. Synlett 2000, 365366.
6. Liu, P.; Jacobsen, E. N. J.Am. Chem. Soc. 2001, 123, 1077210773.
7. Charette, A. B.;Berthelette, C.; St-Martin, D. Tetrahedron Lett. 2001, 42,5149–5153.
8. Alonso, D. A.; Najera, C.;Varea, M. Tetrahedron Lett. 2004, 45, 573–577.
9. Alonso, D. A.; Fuensanta,M.; Najera, C.; Varea, M. J. Org. Chem. 2005, 70, 6404.
10. Rong, F. Julia–Lythgoeolefination. In Name Reactions for Homologations-Part I; Li,
J. J., Ed.; Wiley: Hoboken, NJ,2009, pp 447473. (Review).
11. Davies, S. G.; Fletcher, A.M.; Foster, E. M.; Lee, J. A.; Roberts, P. M.; Thomson, J.
E. J. Org. Chem. 2013,78, 2500–2510.
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