Povarov Reaction. Zain Yousaf 10/22/2013 University of Illinois at Urbana-Champaign
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1 Povarov Reaction Zain Yousaf 10/22/2013 University of Illinois at Urbana-Champaign
2 Contents Introduction Chiral Lewis Acids Bronsted Acid Lanthanide complexes L-ramipril acid derived Sulfonamide Urea Derivative Chiral Phosphoric Acid derivatievs
3 Povarov Reaction Povarov and Mikhailov in 1963 L. S. Povarov and B. M. Mikhailov, Izv. Akad. Nauk. SSSR, Ser. Khim., 1963, ; L.S.Povarov, V.I.Grigos, and B.M.Mikhailov, Izv.Akad. 51. Nauk SSSR, Otd.Khim.Nauk, 2039(1963).
4 Applications Chem. Rev. 2011, 111,
5 Mechanism Stepwise or concerted Chem. Rev. 2011, 111,
6 Stepwise Trapping intermediates. 92:8-97:3 dr Sridharan, V.; Avenda~no, C.; Menendez, J. C. Synthesis 2008, 7, 1039.
7 Diastereoselectivity Sridharan, V.; Avenda~no, C.; Menendez, J. C. Synthesis 2008, 7, 1039.
8 Chiral Auxiliary Prato, 1989 Borrione. E; Prato, M; Scorrano, G; Stivanello, M. J. CHEM. SOC. PERKIN TRANS. I 1989, 2245
9 Catalytic Chiral Lewis Acid Kobayashi, 1996 H. Ishitani and S. Kobayashi, Tetrahedron Lett., 1996, 37,
10 Transition State Kobayashi, 1996 Si H. Ishitani and S. Kobayashi, Tetrahedron Lett., 1996, 37,
11 Avoiding the OH moity Sundararajan, 2001 G. Sundararajan, N. Prabagaran and B. Varghese, Org. Lett., 2001, 3,
12 Rationalizing ee G. Sundararajan, N. Prabagaran and B. Varghese, Org. Lett., 2001, 3,
13 Efficient chiral Lewis Acids Feng, 2010 M. Xie, X. Chen, Y. Zhu, B. Gao, L. Lin, X. Liu and X. Feng, Angew. Chem., Int. Ed., 2010, 49,
14 Quaternary stereocenter at C4 Feng, 2011 M. Xie, X. Liu, Y. Zhu, X. Zhao, Y. Xia, L. Lin and X. Feng, Chem. Eur. J., 2011, 17,
15 Chiral Bronsted Acid Akiyama 2006 T. Akiyama, H. Morita and K. Fuchibe, J. Am. Chem. Soc., 2006, 128,
16 Enecarbamates And Si face Attack Masson and Zhu steps 32% overall yield H. Liu, G. Dagousset, G. Masson, P. Retailleau and J. Zhu, J. Am. Chem. Soc., 2009, 131,
17 Difference is Stereoselectivity H. Liu, G. Dagousset, G. Masson, P. Retailleau and J. Zhu, J. Am. Chem. Soc., 2009, 131,
18 Tri Substituted Quinolines Masson and Zhu 2011 G. Dagousset, J. Zhu and G. Masson, J. Am. Chem. Soc., 2011, 133,
19 Tri Substituted Quinolines G. Dagousset, J. Zhu and G. Masson, J. Am. Chem. Soc., 2011, 133,
20 Sulfonamide Urea Derivative Jacobson 2010 A. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao and E. N. Jacobsen, Science, 2010, 327,
21 Sulfonamide Urea Derivative A. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao and E. N. Jacobsen, Science, 2010, 327,
22 Group Question Figure out if the mechanism is concerted or stepwise using the following infomation? Kinetic isotope effect on hydrogen ortho to aniline is Hammet correlation obtained using aniline substituent ρ = A. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao and E. N. Jacobsen, Science, 2010, 327,
23 Group Answer No primary kinetic isotope effect mean aromatization is fast so d is not part of rate limiting step. Positive hammet correlation consistent with a and c but not b. Small kinetic isotope effect mean rehybradization is part of rate limiting step thus c. A. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao and E. N. Jacobsen, Science, 2010, 327,
24 Vinyl Indoles as dienophiles Bernadi and Ricci 2010 G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi and A. Ricci, Chem. Commun., 2010, 46,
25 3-Vinyl Indoles 3-Vinyl indole G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi and A. Ricci, Chem. Commun., 2010, 46,
26 2-Vinyl Indoles 2-Vinyl indole G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi and A. Ricci, Chem. Commun., 2010, 46,
27 Cyclic tertiary Enethioureas Masson and Zhu 2012 G. Dagousset, P. Retailleau, G. Masson and J. Zhu, Chem. Eur. J., 2012, 18,
28 Cyclic tertiary Enethioureas G. Dagousset, P. Retailleau, G. Masson and J. Zhu, Chem. Eur. J., 2012, 18,
29 Tri substituted quinolines Masson 2012 L. He, M. Bekkaye, P. Retailleau and G. Masson, Org. Lett., 2012, 14,
30 Quaternary stereocenter at C4 Luo and Gong 2012 F. Shi, G.-J. Xing, Z.-L. Tao, S.-W. Luo, S.-J. Tu and L.-Z. Gong, J. Org. Chem., 2012, 77,
31 Quaternary stereocenter at C4 F. Shi, G.-J. Xing, Z.-L. Tao, S.-W. Luo, S.-J. Tu and L.-Z. Gong, J. Org. Chem., 2012, 77,
32 Conclusion Povarov reaction is efficient and highly stereoselective method of constructing 2 to 3 substituted quinolones with large functional group tolerance. 3 different comonents can be fused together in a single step. Can be scaled up with reduction in catalyst loading but usually at the cost of stereoselectivity. Electron rich dienophiles and electron poor anilines and aldehydes necessary to get good yields. Still low yields and ee with aliphatic aldehydes.
33 References Chem. Soc. Rev., 2013, 42, Chem. Rev. 2011, 111, Synthesis. 1993, 535. Russ. Chem. Rev. 1967, 36, 656. Sridharan, V.; Avenda~no, C.; Menendez, J. C. Synthesis 2008, 7, Borrione. E; Prato, M; Scorrano, G; Stivanello, M. J. CHEM. SOC. PERKIN TRANS. I 1989, 2245 H. Ishitani and S. Kobayashi, Tetrahedron Lett., 1996, 37, G. Sundararajan, N. Prabagaran and B. Varghese, Org. Lett., 2001, 3, M. Xie, X. Chen, Y. Zhu, B. Gao, L. Lin, X. Liu and X. Feng, Angew. Chem., Int. Ed., 2010, 49, M. Xie, X. Liu, Y. Zhu, X. Zhao, Y. Xia, L. Lin and X. Feng, Chem. Eur. J., 2011, 17, H. Liu, G. Dagousset, G. Masson, P. Retailleau and J. Zhu, J. Am. Chem. Soc., 2009, 131, G. Dagousset, J. Zhu and G. Masson, J. Am. Chem. Soc., 2011, 133, A. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao and E. N. Jacobsen, Science, 2010, 327, G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi and A. Ricci, Chem. Commun., 2010, 46, G. Dagousset, P. Retailleau, G. Masson and J. Zhu, Chem. Eur. J., 2012, 18, L. He, M. Bekkaye, P. Retailleau and G. Masson, Org. Lett., 2012, 14, F. Shi, G.-J. Xing, Z.-L. Tao, S.-W. Luo, S.-J. Tu and L.-Z. Gong, J. Org. Chem., 2012, 77,
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