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Synlett 2011(12): 1727-1730  
DOI: 10.1055/s-0030-1260773
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Proline-Catalyzed Enantioselective Synthesis of Aza-Quaternary Carbon Derivatives

Liqi Li, Manyi Han, Mingxing Xiao, Zhixiang Xie*
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: xiezx@lzu.edu.cn;
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Publication History

Received 13 March 2011
Publication Date:
21 June 2011 (online)

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Abstract

2-Aryl-3H-indol-3-ones reacted with aldehydes or ketones in the presence of l-proline as a catalyst to give the corresponding aza-quaternary carbon addition product in good yield with moderate to excellent regioselectivity and enantioselectivity. The system was applied to the reaction of 2-(2-bromo-phenyl)-3H-indol-3-one and acetaldehyde to give 2-[2-(2-bromophenyl)-3-oxoindolin-2-yl]acetaldehyde, which is a precursor for the synthesis of some alkaloids such as hinckdentine A.

Key words

aza-quaternary carbon - proline - Mannich reaction - hinckdentine A

    References and Notes

  • 1 In Chiral Amine Synthesis   Nugent TC. Wiley-VCH; Weinheim: 2010. 
    Google Scholar
  • For general reviews, see:
  • 2a Arend M. Westermann B. Risch N. Angew. Chem. Int. Ed.  1998,  37:  1044 
    Google Scholar
  • 2b Bur SK. Martin SF. Tetrahedron  2001,  57:  3221 
    Google Scholar
  • 2c Córdova A. Acc. Chem. Res.  2004,  37:  102 
    Google Scholar
  • 3a Saaby S. Nakama K. Lie MA. Hazell RG. Jørgensen KA. Chem. Eur. J.  2003,  9:  6145 
    Google Scholar
  • 3b Zhuang W. Saaby S. Jørgensen KA. Angew. Chem. Int. Ed.  2004,  43:  4476 
    Google Scholar
  • For reviews, see:
  • 4a List B. Tetrahedron  2002,  58:  5573 
    Google Scholar
  • 4b List B. Acc. Chem. Res.  2004,  37:  548 
    Google Scholar
  • 4c Notz W. Tanaka F. Barbas CF. Acc. Chem. Res.  2004,  37:  580 
    Google Scholar
  • 4d Dalko PI. Moisan L. Angew. Chem. Int. Ed.  2004,  43:  5138 
    Google Scholar
  • 5 Xie ZX. Zhang LZ. Ren XJ. Tang SY. Li Y. Chin. J. Chem.  2008,  26:  1272 
    CrossrefGoogle Scholar
  • 6a List B. J. Am. Chem. Soc.  2000,  122:  9336 
    Google Scholar
  • 6b List B. Pojarliev P. Biller WT. Martin HJ. J. Am. Chem. Soc.  2002,  124:  827 
    Google Scholar
  • 7a Notz W. Sakthivel K. Bui T. Zhong G. Barbas CF. Tetrahedron Lett.  2001,  42:  199 
    Google Scholar
  • 7b Cordova A. Notz W. Zhong G. Betancort JM. Barbas CF.
    J. Am. Chem. Soc.  2002,  124:  1842 
    Google Scholar
  • 7c Cordova A. Watanabe S.-I. Tanaka F. Notz W. Barbas CF.
    J. Am. Chem. Soc.  2002,  124:  1866 
    Google Scholar
  • 8a Munch A. Wendt B. Christmann M. Synlett  2004,  2751 
    Google Scholar
  • 8b Ibrahem I. Casas J. Cordova A. Angew. Chem. Int. Ed.  2004,  43:  6528 
    Google Scholar
  • 8c Cobb AJA. Shaw DM. Longbottom DA. Gold JB. Ley SV. Org. Biomol. Chem.  2005,  3:  84 
    Google Scholar
  • 9 Hayashi Y. Tsuboi W. Shoji M. Suzuki N. J. Am. Chem. Soc.  2003,  125:  11208 
    CrossrefGoogle Scholar
  • 10a Rodriguez B. Bolm C. J. Org. Chem.  2006,  71:  2888 
    Google Scholar
  • 10b Ibrahem I. Cordova A. Tetrahedron Lett.  2005,  46:  3363 
    Google Scholar
  • 10c Westermann B. Neuhaus C. Angew. Chem. Int. Ed.  2005,  44:  4077 
    Google Scholar
  • 11 Chowdari NS. Ramachary DB. Barbas CF. Synlett  2003,  1906 
    Article in Thieme ConnectGoogle Scholar
  • 12 Kantam ML. Rajasekhar ChV. Gopikrishna G. Reddya KR. Choudaryb BM. Tetrahedron Lett.  2006,  47:  5965 
    CrossrefGoogle Scholar
  • 13 Liu J.-F. Jiang Z.-Y. Wang R.-R. Zeng Y.-T. Chen J.-J. Zhang X.-M. Ma Y.-B. Org. Lett.  2007,  9:  4127 
    CrossrefGoogle Scholar
  • 14 Blackman AJ. Hambley TW. Picker K. Taylor WC. Thirasasana N. Tetrahedron Lett.  1987,  28:  5561 
    CrossrefGoogle Scholar
  • 15 Astolfi P. Panagiotaki M. Rizzoli C. Greci L. Org. Biomol. Chem.  2006,  4:  3282 
    CrossrefGoogle Scholar
  • 17a Barnwell N. Beddoes RL. Mitchell MB. Joule JA. Heterocycles  1994,  37:  175 
    Google Scholar
  • 17b Billimoria AD. Cava MP. J. Org. Chem.  1994,  59:  6777 
    Google Scholar
  • 17c Billimoria AD. Cava MP. Heterocycles  1996,  42:  453 
    Google Scholar
  • 17d Liu YH. McWhorter WW. J. Am. Chem. Soc.  2003,  125:  4240 
    Google Scholar
  • 17e Higuchi K. SatoY . Tsuchimochi M. Sugiura K. Hatori M. Kawasaki T. Org. Lett.  2009,  11:  197 
    Google Scholar
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CCDC 815953 (for 3h) and CCDC 815954 (for 3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/deposit [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax +44 (1223)336033; email: deposit@ccdc.cam.ac.uk].