不对称催化的烯烃卤化反应课件精品.pptVIP

不对称催化的烯烃卤化反应 陶忠林 2012/11/24 1. Introduction 2. Chiral Lewis Base Catalysis 3. Chiral Ion Pairing Catalysis 4. Hydrogen Bonding 5. Lewis Acid Catalysis 6. Conclusion 1. Introduction olefin-to-olefin transfer Catalysis model Scott E. Denmark, Angew. Chem. Int. Ed. 2012, 51, 10938 – 10953 2. Chiral Lewis Base Catalysis K. Ishihara, Nature 2007, 445, 900 – 903. N. Shibata, Angew. Chem.Int. Ed. 2008, 47, 4157 - 4161. V. Gouverneur, Angew. Chem. Int. Ed. 2011, 50, 8105 –8109 E. N. Jacobsen, Angew. Chem. Int. Ed. 2010, 49, 7332 –7335 3. Chiral Ion Pairing Catalysis R. Fr?hlich, Org. Lett. 2011, 13, 860–863. L. X. Gao, J. Org. Chem. 2004, 69, 2874-2876 Y. Shi, Org.Lett. 2011, 13, 6350 – 6353. S. E. Denmark, Org. Lett. 2012, 14, 256 – 259. F. D. Toste, Science，2011, 334, 1681 – 1684 Z. Tang, Tetrahedron Asymmetry. 2012 , 23, 245–251 J. N. Johnston, J. Am. Chem. Soc. 2012, 134, 6068?6071 4.Hydrogen Bonding B. Borhan, J. Am. Chem. Soc. 2010, 132, 3298–3300 B. Borhan, J. Am. Chem. Soc. 2010, 132, 3298–3300 W. Tang, J. Am. Chem. Soc. 2010, 132, 3664-3665. 将cat与NBS在溶剂中搅拌20min,再加入反应物： 收率不变，85%ee降为54%； 将cat与NBS在溶剂中搅拌4h,再加入反应物： 收率不变，85%ee降为26%. R1=R3=H,R2=Cl时，DABCO或者BnNHC(O)NHTs单独加，NR。 Y-Y Yeung J. Am. Chem. Soc. 2010, 132, 15474–15476 Y-Y Yeung, Angew. Chem. Int. Ed. 2012, 51, 7771 –7775 Y-Y Yeung J. Am. Chem. Soc. 2011, 133, 9164–9167 Y-Y Yeung Chem. Commun., 2012, 48, 5793–5795 Y-Y Yeung Org. Biomol. Chem., 2012, 10, 3808–3811 K. C. Nicolaou, J. Am. Chem. Soc. 2011, 133, 8134–8137 H. Fujioka, Angew. Chem. Int. Ed. 2010, 49, 9174 –9177 H. Fujioka, Chem. Eur. J. 2012, 18, 8448 – 8453 B. Borhan Angew. Chem. Int. Ed. 2011, 50, 2593 –2596 S. J. Miller, Science 2010, 328, 1251 –1255. Y. Q. Tu, J. Am. Chem. Soc. 2011, 133, 8818–8821 Y. Q. Tu, Chem. Sci. 2011, 2, 1839 –1841 U. Hennecke, Synlett 2011, 2043 – 2047. S. F. Martin, J. Am. Chem. Soc. 2012, 134, 11128?11131 T. Taguchi, Tetrahedron Let, 1995, 36, 9333-9336 T. Taguchi, J. Org. Chem. 1997, 62, 7384-7389 S. H. Ka