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Synthesis 2009(23): 3994-4000  
DOI: 10.1055/s-0029-1217038
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Friedel-Crafts Alkylation of Indoles with Aromatic α,β-Unsaturated Aldehydes Catalyzed by Diphenylprolinol Silyl Ether

Zhi-Jing Wanga, Jian-Guo Yangb, Jun Jina, Xin Lva, Weiliang Bao*a
a Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. of China
Fax: +86(571)88273814; e-Mail: wlbao@css.zju.edu.cn;
b Office of Assets Administration, Taizhou University, Linhai 317000, P. R. of China
Further Information

Publication History

Received 15 June 2009
Publication Date:
12 October 2009 (online)

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Abstract

A catalytic enantioselective Friedel-Crafts alkylation of indoles with aromatic α,β-unsaturated aldehydes has been developed. The process is promoted by (S)-diphenylprolinol trimethyl silyl ether to afford, after sodium borohydride mediated reduction, 3-indolyl-3-phenylpropanols in high enantioselectivities and good yields.

Key words

organocatalysis - enantioselectivity - Friedel-Crafts alkylation - indoles - aromatic α,β-unsaturated aldehydes

    References

  • 1 For a review, see: Olah GA. Khrisnamurti R. Surya Prakashi GK. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Pergamon; New York: 1991.  p.293 
    Google Scholar
  • 2a Sundberg RJ. Indoles   Academic Press; San Diego: 1996.  p.175 
    Google Scholar
  • 2b Nicolaou KC. Snyder SA. Classics in Total Synthesis II   Wiley-VCH; Weinheim: 2003. 
    Google Scholar
  • For selected metal-catalyzed procedures, see:
  • 3a Jensen KB. Thorbauge J. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed.  2001,  40:  160 
    Google Scholar
  • 3b Zhou J. Tang Y. J. Am. Chem. Soc.  2002,  124:  9030 
    Google Scholar
  • 3c Evans DA. Scheidt KA. Fandrick KR. Lam HW. Wu J. J. Am. Chem. Soc.  2003,  125:  10780 
    Google Scholar
  • 3d Lyle MPA. Draper ND. Wilson PD. Org. Lett.  2005,  7:  901 
    Google Scholar
  • 3e Palomo C. Oiarbide M. Kardak BG. Garcia JM. Linden A. J. Am. Chem. Soc.  2005,  127:  4154 
    Google Scholar
  • 3f Evans DA. Fandrick KR. Song H. J. Am. Chem. Soc.  2005,  127:  8942 
    Google Scholar
  • 3g Takenaka N. Abell JP. Yamamoto H. J. Am. Chem. Soc.  2007,  129:  742 
    Google Scholar
  • 3h Arai T. Yokoyama N. Yanagisawa A. Chem. Eur. J.  2008,  14:  2052 
    Google Scholar
  • 3i Arai T. Yokoyama N. Angew. Chem. Int. Ed.  2008,  47:  4989 
    Google Scholar
  • For recent reviews on organocatalysis, see for example:
  • 4a Dalko PL. Moisan L. Angew. Chem. Int. Ed.  2004,  43:  5138 
    Google Scholar
  • 4b Seayed J. List B. Org. Biomol. Chem.  2005,  3:  719 
    Google Scholar
  • 4c Dalko PI. Enantioselective Organocatalysis   Wiley-VCH; Weinheim: 2007. 
    Google Scholar
  • 4d Pellissier H. Tetrahedron  2007,  63:  9267 
    Google Scholar
  • 4e Dondoni A. Massi A. Angew. Chem. Int. Ed.  2008,  47:  4638 
    Google Scholar
  • 5 Austin JF. MacMillan DWC. J. Am. Chem. Soc.  2002,  124:  1172 
    CrossrefGoogle Scholar
  • 6a Austin JF. Kim S.-G. Sinz CJ. Xiao W.-J. MacMillan DWC. Proc. Natl. Acad. Sci. U.S.A.  2004,  101:  5482 
    Google Scholar
  • 6b King HD. Meng Z. Denhart D. Mattson R. Kimura R. Wu W. Gao Q. Macor JE. Org. Lett.  2005,  7:  3437 
    Google Scholar
  • 6c Bonini BF. Capitò E. Comes-Franchini M. Fochi M. Ricci A. Zwanenburg B. Tetrahedron: Asymmetry  2006,  17:  3135 
    Google Scholar
  • 6d Li C. Liu H. Liao J. Cao Y. Liu X. Xiao W. Org. Lett.  2007,  9:  1847 
    Google Scholar
  • 7a Herrera RP. Sgarzani V. Bernardi L. Ricci A. Angew. Chem. Int. Ed.  2005,  44:  6576 
    Google Scholar
  • 7b Fleming EM. McCabe T. Connon SJ. Tetrahedron Lett.  2006,  47:  7037 
    Google Scholar
  • 7c Itoh J. Fuchibe K. Akiyama T. Angew. Chem. Int. Ed.  2008,  47:  4016 
    Google Scholar
  • 7d Ganesh M. Seidel D. J. Am. Chem. Soc.  2008,  130:  16464 
    Google Scholar
  • 8a Li D.-P. Guo Y.-C. Ding Y. Xiao W.-J. Chem. Commun.  2006,  799 
    Google Scholar
  • 8b Bartoli G. Bosco M. Carlone A. Pesciaioli F. Sambri L. Melchiorre P. Org. Lett.  2007,  9:  1403 
    Google Scholar
  • 8c Tang H.-Y. Lu A.-D. Zhou Z.-H. Zhao G.-F. He L.-N. Tang C.-C. Eur. J. Org. Chem.  2008,  1406 
    Google Scholar
  • 9a Wang Y.-Q. Song J. Hong R. Li H. Deng L. J. Am. Chem. Soc.  2006,  128:  8156 
    Google Scholar
  • 9b Kang Q. Zhao Z.-A. You S.-L. J. Am. Chem. Soc.  2007,  129:  1484 
    Google Scholar
  • 9c Rowland GB. Rowland EB. Liang Y. Perman JA. Antilla JC. Org. Lett.  2007,  9:  2609 
    Google Scholar
  • 9d Wanner MJ. Hauwert P. Schoemaker HE. de Gelder R. van Maarseveen JH. Hiemstra H. Eur. J. Org. Chem.  2008,  180 
    Google Scholar
  • 10 Török B. Abid M. London G. Esquibel J. Török M. Mhadgut SC. Yan P. Prakash GKS. Angew. Chem. Int. Ed.  2005,  44:  3086 
    CrossrefPubMedGoogle Scholar
  • 11 Terada M. Sorimachi K. J. Am. Chem. Soc.  2007,  129:  292 
    CrossrefGoogle Scholar
  • For the first reports on the use of diarylprolinol silyl ethers, see:
  • 12a Marigo M. Wabnitz TC. Fielenbach D. Jørgensen KA. Angew. Chem. Int. Ed.  2005,  44:  794 
    Google Scholar
  • 12b Marigo M. Fielenbach D. Braunton A. Kjasgaard A. Jørgensen KA. Angew. Chem. Int. Ed.  2005,  44:  3703 
    Google Scholar
  • 12c Hayashi Y. Gotoh H. Hayashi T. Shoji M. Angew. Chem. Int. Ed.  2005,  44:  4212 
    Google Scholar
  • For selected diarylprolinol silyl ethers catalyzed α-func­-tionalization of aldehydes, see:
  • 13a Mossé S. Alexakis A. Org. Lett.  2005,  7:  4361 
    Google Scholar
  • 13b Chi Y. Gellman SH. J. Am. Chem. Soc.  2006,  128:  6804 
    Google Scholar
  • 13c Ibrahem I. Zhao G.-L. Cordóva A. Chem. Eur. J.  2007,  13:  683 
    Google Scholar
  • 13d Aleman J. Cabrera S. Maerten E. Overgaard J. Jørgensen KA. Angew. Chem. Int. Ed.  2007,  46:  5520 
    Google Scholar
  • 13e Tiecco M. Carlone A. Sternativo S. Marini F. Bartoli G. Melchiorre P. Angew. Chem. Int. Ed.  2007,  46:  6882 
    Google Scholar
  • 13f Palomo C. Vera S. Velila I. Mielgo A. Gomez-Bengoa E. Angew. Chem. Int. Ed.  2007,  46:  8054 
    Google Scholar
  • 13g Hayashi Y. Itoh T. Ohkubo M. Ishikawa H. Angew. Chem. Int. Ed.  2008,  47:  4722 
    Google Scholar
  • 13h Chi Y. Guo L. Kopf NA. Gellman SH. J. Am. Chem. Soc.  2008,  130:  5608 
    Google Scholar
  • 13i Shibatomi K. Yamamoto H. Angew. Chem. Int. Ed.  2008,  47:  5796 
    Google Scholar
  • For selected diarylprolinol silyl ethers catalyzed β-func-tionalization and γ-functionalization of α,β-unsaturated aldehydes, see:
  • 14a Marigo M. Schulte T. Franzen J. Jørgensen KA. J. Am. Chem. Soc.  2005,  127:  15710 
    Google Scholar
  • 14b Gotoh H. Masui R. Ogino H. Shoji M. Hayashi Y. Angew. Chem. Int. Ed.  2006,  45:  6853 
    Google Scholar
  • 14c Ibrahem I. Rios R. Vesely J. Zhao G. Cordóva A. Chem. Commun.  2007,  849 
    Google Scholar
  • 14d Carlone A. Bartoli G. Bosco M. Sambri L. Melchiorre P. Angew. Chem. Int. Ed.  2007,  46:  4504 
    Google Scholar
  • 14e Ibrahem I. Rios R. Vesely J. Hammar P. Eriksson L. Himo F. Cordóva A. Angew. Chem. Int. Ed.  2007,  46:  4507 
    Google Scholar
  • 14f Wang Y. Li P. Liang X. Zhang TY. Ye J. Chem. Commun.  2008,  1232 
    Google Scholar
  • 14g Hayashi Y. Samanta S. Gotoh H. Ishikawa H. Angew. Chem. Int. Ed.  2008,  47:  6634 
    Google Scholar
  • 14h Zhao G.-L. Rios R. Vesely J. Eriksson L. Cordóva A. Angew. Chem. Int. Ed.  2008,  47:  8468 
    Google Scholar
  • For selected diarylprolinol silyl ethers catalyzed cascade, tandem, domino and multicomponent reactions, see:
  • 15a Enders D. Huttl MRM. Grondal C. Raabe G. Nature  2006,  441:  861 
    Google Scholar
  • 15b Brandau S. Maerten E. Jørgensen KA. J. Am. Chem. Soc.  2006,  128:  14986 
    Google Scholar
  • 15c Hayashi Y. Okano T. Aratake S. Hazelard D. Angew. Chem. Int. Ed.  2007,  46:  4922 
    Google Scholar
  • 15d Reyes E. Jiang H. Milelli A. Elsner P. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed.  2007,  46:  9202 
    Google Scholar
  • 15e Sunden H. Rios R. Ibrahem I. Zhao G. Eriksson L. Cordóva A. Adv. Synth. Catal.  2007,  349:  827 
    Google Scholar
  • 15f Xie H. Zu L. Li H. Wang J. Wang W. J. Am. Chem. Soc.  2007,  129:  10886 
    Google Scholar
  • 15g Cabrera S. Aleman J. Bolze P. Bertelsen S. Jørgensen KA. Angew. Chem. Int. Ed.  2008,  47:  121 
    Google Scholar
  • 15h Hayashi Y. Gotoh H. Masui R. Ishikawa H. Angew. Chem. Int. Ed.  2008,  47:  4012 
    Google Scholar
  • 15i Enders D. Wang C. Bats JW. Angew. Chem. Int. Ed.  2008,  47:  7539 
    Google Scholar
  • For recent reviews on diarylprolinol silyl ethers, see:
  • 16a Palomo C. Mielgo A. Angew. Chem. Int. Ed.  2006,  45:  7876 
    Google Scholar
  • 16b Mielgo A. Palomo C. Chem. Asian J.  2008,  3:  922 
    Google Scholar
  • 17 After our original submission of this manuscript to another journal on the 11th of March, a paper by Wang and co-workers appeared on the web on 17th March, see: Hong L. Wang L. Chen C. Zhang B. Wang R. Adv. Synth. Catal.  2009,  351:  772 
    CrossrefGoogle Scholar