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不对称交叉偶联反应

不对称交叉偶联反应. 陶忠林 2012/06/16. 1.介绍 2 . sp2-sp2 的不对称交叉偶联 3 . 含 sp3 碳的不对称交叉偶联反应 4 . 总结. 1. 主要内容. 不包括 Heck 反应以及烯丙基话反应. 2. sp2-sp2 的不对称交叉偶联 手性联萘骨架在不对称合成中具有重要作用。. Hayashi, T. J. Am. Chem. S oc . 1988 , 110 , 8153-8156. Hayashi, T. J. Am. Chem. S oc . 1995, 117, 9101-9102.

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不对称交叉偶联反应

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  1. 不对称交叉偶联反应 陶忠林 2012/06/16

  2. 1.介绍 2. sp2-sp2的不对称交叉偶联 3.含sp3碳的不对称交叉偶联反应 4.总结

  3. 1.主要内容 不包括Heck反应以及烯丙基话反应

  4. 2. sp2-sp2的不对称交叉偶联 手性联萘骨架在不对称合成中具有重要作用。

  5. Hayashi, T.J. Am. Chem. Soc. 1988, 110, 8153-8156 Hayashi, T.J. Am. Chem. Soc.1995,117, 9101-9102

  6. Hayashi, T. Tetrahedron Lett. 1996 , 37, 3161-3164 Hayashi, T.Tetrahedron1999, 55, 3455-3466 Shibasaki, M. Tetrahedron: Asymmetry1998, 9, 3751–3754

  7. Buchwald, S.L J. Am. Chem. Soc. 2000,122, 12051-12052 Buchwald, S.L J. Am. Chem. Soc. 2010,132, 11278-11287 Cammidge, A. N. Chem. Commun., 2000, 1723–1724

  8. Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396-13397 Hayashi, T. J. Org. Chem. 2004, 69, 3811-3823 Johannsen, M. Org. Lett.2003, 5,3025-3028

  9. Baudoin, O. J. Org. Chem. 2003, 68, 4897-4905 Mikami, K. Chem. Commun. 2004 , 2082–2083

  10. Cammidge, A.N. Tetrahedron2004,60, 4377–4386 Espinet, P. Chem. Eur. J. 2006, 12, 9346–9352

  11. Espinet, P. Tetrahedron: Asymmetry2007,18, 625–627 Fernández, R. J. Am. Chem. Soc. 2008, 130, 15798–15799

  12. Fujihara, H. Angew. Chem. Int. Ed. 2008, 47, 6917–6919 Uozumi, Y. Angew. Chem. Int. Ed.2009, 48, 2708–2710

  13. Lin, G.Q.Org. Lett.2010, 12, 5546-5549 Suginome, M. Angew. Chem. Int. Ed.2011, 50, 8844 –8847

  14. Qiu, L.Q.Org. Lett. 2012, 14, 1966–1969 Shibata, T. Chem. Commun. 2009, 1870–1872

  15. 3 .含sp3碳的不对称交叉偶联反应 Kumada, M. J. Am. Chem. Soc. 1976,98, 3718-3719 Kumada, M. J. Am. Chem. Soc.1982. 104, 180-186 Nagel, U.Chem. Ber./Recueil1997, 130, 535-542

  16. Aoyama, T. Tetrahedron2004, 60, 10701–10709 1).体系具有较好的选择性，能够兼容非活泼一级或者二级溴代物; 2).当加入0.8 eq 锌试剂时，未反应的溴代物的ee值为0，反应不存在拆分。 Fu, G.C. J. Am. Chem. Soc. 2005, 127, 4594-4595

  17. 反应对水和氧并不十分敏感 反应条件下，苯环上的Cl不参与反应。 不存在拆分现象 Fu, G.C. J. Am. Chem. Soc. 2005, 127, 10482-10483 R1和R3相同时，不存在区域选择性问题； R1和R3为不同烷基时，区域选择性较差； R1为吸电子基团，R3为烷基时，选择性较好。 Fu, G.C. J. Am. Chem. Soc. 2008, 130, 2756-2757

  18. Fu, G.C. J. Am. Chem. Soc. 2008, 130, 3302-3303 Fu, G.C. J. Am. Chem. Soc. 2008, 130, 6694–6695

  19. Fu, G.C. J. Am. Chem. Soc. 2008, 130, 12645–12647 Fu, G.C. Angew. Chem. Int. Ed.2009, 48, 154 –156

  20. Fu, G.C. J. Am. Chem. Soc. 2010,132, 1264–1266 Fu, G.C. J. Am. Chem. Soc. 2010, 132, 5010–5011

  21. Fu, G.C. J. Am. Chem. Soc. 2010, 132, 11027–11029 Fu, G.C. J. Am. Chem. Soc. 2010,132, 11908–11909

  22. Fu, G.C. J. Am. Chem. Soc. 2011, 133, 8154–8157 Fu, G.C. J. Am. Chem. Soc. 2011, 133, 15362–15364

  23. Fu, G.C. J. Am. Chem. Soc.2012,134, 5794−5797 Fu, G.C. J. Am. Chem. Soc. 2012, 134, 9102−9105

  24. Fu, G.C. J. Am. Chem.Soc. 2012, 134, 2966−2969 非活泼卤代物的机理

  25. 4.总结 1.Sp2与Sp2或者Sp的偶联研究的比较多，得到的联萘骨架的产物在不对称合成中具有较多运用。 2.含sp3碳的不对称偶联反应主要是Fu的Ni体系，研究的相对较少。新的体系有待发展。

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