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Novel Chiral Secondary Amine-Amide Catalysts Friedel-Craft Alkylation Reaction
Corresponding Author(s) : Zhiming Chen
Asian Journal of Chemistry,
Vol. 29 No. 3 (2017): Vol 29 Issue 3
Abstract
A highly efficient catalytic asymmetric Friedel-Crafts alkylation of indole with nitroalkenes using novel chiral secondary amine-amide as catalyst has been developed. Various types of nitroalkylated indoles were obtained in excellent yields (81-93 %) and high enantio-selectivities (up to 95 % ee).
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- M. Bandini and A. Umani-Ronchi, Catalytic Asymmetric Friedel-Crafts Alkylations, Wiley-VCH: Weinheim, Germany (2009).
- For selected reviews, see: M. Bandini, A. Melloni and A. Umani-Ronchi, Angew. Chem. Int. Ed., 43, 550 (2004).
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- S.-L. You, Q. Cai and M. Zeng, Chem. Soc. Rev., 38, 2190 (2009).
- V. Terrasson, R.M. de Figueiredo and J.M. Campagne, Eur. J. Org. Chem., 2010, 2635 (2010).
- R.P. Herrera, V. Sgarzani, L. Bernardi and A. Ricci, Angew. Chem. Int. Ed., 44, 6576 (2005).
- W. Zhuang, R.G. Hazell and K.A. Jørgensen, Org. Biomol. Chem., 3, 2566 (2005).
- K.B. Jensen, J. Thorhauge, R.G. Hazell and K.A. Jørgensen, Angew. Chem. Int. Ed., 40, 160 (2001).
- W. Zhuang, N. Gathergood, R.G. Hazell and K.A. Jørgensen, J. Org. Chem., 66, 1009 (2001).
- N.A. Paras and D.W.C. MacMillan, J. Am. Chem. Soc., 124, 7894 (2002).
- J. Zhou and Y. Tang, J. Am. Chem. Soc., 124, 9030 (2002).
- D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev., 103, 893 (2003).
- S. Cacchi and G. Fabrizi, Chem. Rev., 105, 2873 (2005).
- S.F. Lu, D.M. Du, J. Xu, Org. Lett., 8, 2115 (2008).
- J. Weng, R.-J. Fan, Q.-M. Deng, R.-R. Liu, J.-R. Gao and Y.-X. Jia, J. Org. Chem., 81, 3023 (2016).
- D. Enders, P. Fey and H. Kipphardt, Org. Synth., 65, 173 (1988).
- A.F. Spatola, M.K. Anwer, A.L. Rockwell and L.M. Gierasch, J. Am. Chem. Soc., 108, 825 (1986).
- G.W. Kabalka, M. Varma, R.S. Varma, P.C. Srivastava and F.F. Knapp, J. Org. Chem., 51, 2386 (1986).
- N. Dahlin, A. Bøgevig and H. Adolfsson, Adv. Synth. Catal., 346, 1101 (2004).
- H. Iwamura, S.P. Mathew and D.G. Blackmond, J. Am. Chem. Soc., 126, 11770 (2004).
- S. Lee and D.W.C. MacMillan, J. Am. Chem. Soc., 129, 15438 (2007).
- Y.-Z. Liu, R.-L. Cheng and P.-F. Xu, Org. Chem., 76, 2884 (2011).
- C.C. Wang, S.L. Xie and Z.F. Xie, Chinese J. Org. Chem., 33, 1919 (2013).
- J. Xie, X. Zhu, M. Huang, F. Meng, M. Wang and Y. Wan, Synth. Commun., 40, 3259 (2010).
References
M. Bandini and A. Umani-Ronchi, Catalytic Asymmetric Friedel-Crafts Alkylations, Wiley-VCH: Weinheim, Germany (2009).
For selected reviews, see: M. Bandini, A. Melloni and A. Umani-Ronchi, Angew. Chem. Int. Ed., 43, 550 (2004).
T.B. Poulsen and K.A. Jørgensen, Chem. Rev., 108, 2903 (2008).
S.-L. You, Q. Cai and M. Zeng, Chem. Soc. Rev., 38, 2190 (2009).
V. Terrasson, R.M. de Figueiredo and J.M. Campagne, Eur. J. Org. Chem., 2010, 2635 (2010).
R.P. Herrera, V. Sgarzani, L. Bernardi and A. Ricci, Angew. Chem. Int. Ed., 44, 6576 (2005).
W. Zhuang, R.G. Hazell and K.A. Jørgensen, Org. Biomol. Chem., 3, 2566 (2005).
K.B. Jensen, J. Thorhauge, R.G. Hazell and K.A. Jørgensen, Angew. Chem. Int. Ed., 40, 160 (2001).
W. Zhuang, N. Gathergood, R.G. Hazell and K.A. Jørgensen, J. Org. Chem., 66, 1009 (2001).
N.A. Paras and D.W.C. MacMillan, J. Am. Chem. Soc., 124, 7894 (2002).
J. Zhou and Y. Tang, J. Am. Chem. Soc., 124, 9030 (2002).
D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev., 103, 893 (2003).
S. Cacchi and G. Fabrizi, Chem. Rev., 105, 2873 (2005).
S.F. Lu, D.M. Du, J. Xu, Org. Lett., 8, 2115 (2008).
J. Weng, R.-J. Fan, Q.-M. Deng, R.-R. Liu, J.-R. Gao and Y.-X. Jia, J. Org. Chem., 81, 3023 (2016).
D. Enders, P. Fey and H. Kipphardt, Org. Synth., 65, 173 (1988).
A.F. Spatola, M.K. Anwer, A.L. Rockwell and L.M. Gierasch, J. Am. Chem. Soc., 108, 825 (1986).
G.W. Kabalka, M. Varma, R.S. Varma, P.C. Srivastava and F.F. Knapp, J. Org. Chem., 51, 2386 (1986).
N. Dahlin, A. Bøgevig and H. Adolfsson, Adv. Synth. Catal., 346, 1101 (2004).
H. Iwamura, S.P. Mathew and D.G. Blackmond, J. Am. Chem. Soc., 126, 11770 (2004).
S. Lee and D.W.C. MacMillan, J. Am. Chem. Soc., 129, 15438 (2007).
Y.-Z. Liu, R.-L. Cheng and P.-F. Xu, Org. Chem., 76, 2884 (2011).
C.C. Wang, S.L. Xie and Z.F. Xie, Chinese J. Org. Chem., 33, 1919 (2013).
J. Xie, X. Zhu, M. Huang, F. Meng, M. Wang and Y. Wan, Synth. Commun., 40, 3259 (2010).