Download PDF
Synthesis 2011(12): 1847-1852  
DOI: 10.1055/s-0030-1260463
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Conjugate Additions of Acetylacetone to 3-Ylideneoxindoles: A Direct Access to Highly Enantioenriched Oxindole Derivatives

Shu-Wen Duan, Hai-Hua Lu, Fu-Gen Zhang, Jun Xuan, Jia-Rong Chen, Wen-Jing Xiao*
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China
Fax: +86(27)67862041; e-Mail: wxiao@mail.ccnu.edu.cn;
Further Information

Publication History

Received 15 March 2011
Publication Date:
13 May 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A highly enantioselective organocatalytic conjugate addition of acetylacetone to 3-ylideneoxindoles is described. This method provides polysubstituted oxindoles in good to excellent enantioselectivities and high isolated yields.

Key words

organocatalysis - bifunctional activation - oxindole - conjugate addition - 3-ylideneoxindole

    References

  • For selected examples, see:
  • 1a Reisman SE. Ready JM. Weiss MM. Hasuoka A. Hirata M. Tamaki K. Ovaska TV. Smith CJ. Wood JL. J. Am. Chem. Soc.  2008,  130:  2087 
    Google Scholar
  • 1b Franz AK. Dreyfuss PD. Schreiber SL. J. Am. Chem. Soc.  2007,  129:  1020 
    Google Scholar
  • 1c Lerchner A. Carreira E. Chem. Eur. J.  2006,  12:  8208 
    Google Scholar
  • 1d Albrecht BK. Williams RM. Org. Lett.  2003,  5:  197 
    Google Scholar
  • 1e Nicolaou KC. Rao PB. Hao J. Reddy MV. Rassias G. Huang X. Chen DY.-K. Snyder SA. Angew. Chem. Int. Ed.  2003,  42:  1753 
    Google Scholar
  • 1f Wearing XZ. Cook JM. Org. Lett.  2002,  4:  4237 
    Google Scholar
  • 1g Bagul TD. Lakshmaiah G. Kawabata T. Fuji K. Org. Lett.  2002,  4:  249 
    Google Scholar
  • 1h Malinakova HC. Liebeskind LS. Org. Lett.  2000,  2:  4083 
    Google Scholar
  • For selected examples, see:
  • 2a Ding K. Lu Y.-P. Nikolovska-Coleska Z. Qiu S. Ding YS. Gao W. Stuckey J. Krajewski K. Roller PP. Tomita Y. Parrish DA. Deschamps JR. Wang S.-M. J. Am. Chem. Soc.  2005,  127:  10130 
    Google Scholar
  • 2b Hewawasam P. Erway M. Moon SL. Knipe J. Weiner H. Boissard CG. Post-Munson DJ. Gao Q. Huang S. Gribkoff VK. Meanwell NA.
    J. Med. Chem.  2002,  45:  1487 
    Google Scholar
  • 2c Tokunaga T. Hume WE. Umezome T. Okazaki K. Ueki Y. Kumagai K. Hourai S. Nagamine J. Seki H. Taiji M. Noguchi H. Nagata R. J. Med. Chem.  2001,  44:  4641 
    Google Scholar
  • 3a Edmondson SD. Danishefsky SJ. Angew. Chem. Int. Ed.  1998,  37:  1138 
    Google Scholar
  • 3b Cui C.-B. Kakeya H. Osada H. Tetrahedron  1997,  53:  59 
    Google Scholar
  • 3c Cui C.-B. Kakeya H. Osada H. Tetrahedron  1996,  52:  12651 
    Google Scholar
  • 4a Carle JS. Christophersen C. J. Org. Chem.  1980,  45:  1586 
    Google Scholar
  • 4b Carle JS. Christophersen C. J. Am. Chem. Soc.  1979,  101:  4012 
    Google Scholar
  • For asymmetric Heck reactions, see:
  • 5a Dounay AB. Overman LE. Chem. Rev.  2003,  103:  2945 
    Google Scholar
  • For selected examples, see:
  • 5b Ruck RT. Huffman MA. Kim MM. Shevlin M. Kandur WV. Davies IW. Angew. Chem. Int. Ed.  2008,  47:  4711 
    Google Scholar
  • 5c Dounay AB. Hatanaka K. Kodanko JJ. Oestreich M. Overman LE. Pfeifer LA. Weiss MM. J. Am. Chem. Soc.  2003,  125:  6261 
    Google Scholar
  • For selected asymmetric aldol reactions, see:
  • 6a Hanhan NV. Sahin AH. Chang TW. Fettinger JC. Franz AK. Angew. Chem. Int. Ed.  2010,  49:  744 
    Google Scholar
  • 6b Ellis JM. Overman LE. Tanner HR. Wang J. J. Org. Chem.  2008,  73:  9151 
    Google Scholar
  • 6c Chen J.-R. Liu X.-P. Zhu X.-Y. Li L. Qiao Y.-F. Zhang J.-M. Xiao W.-J. Tetrahedron  2007,  63:  10437 
    Google Scholar
  • 6d Ogawa S. Shibata N. Inagaki J. Nakamura S. Toru T. Shiro M. Angew. Chem. Int. Ed.  2007,  46:  8666 
    Google Scholar
  • For selected asymmetric alkylation reactions, see:
  • 7a Trost BM. Zhang Y. Chem. Eur. J.  2011,  17:  2916 
    Google Scholar
  • 7b Vyas DJ. Fröhlich R. Oestreich M. J. Org. Chem.  2010,  75:  6720 
    Google Scholar
  • 7c Ma S. Han X.-Q. Krishnan S. Virgil SC. Stoltz BM. Angew. Chem. Int. Ed.  2009,  48:  8037 
    Google Scholar
  • 7d Trost BM. Zhang Y. J. Am. Chem. Soc.  2007,  129:  14548 
    Google Scholar
  • 7e Trost BM. Zhang Y. J. Am. Chem. Soc.  2006,  128:  4590 
    Google Scholar
  • 7f Trost BM. Frederiksen MU. Angew. Chem. Int. Ed.  2004,  43:  308 
    Google Scholar
  • For selected asymmetric hydroxylation reaction, see:
  • 8a Sano D. Nagata K. Itoh T. Org. Lett.  2008,  10:  1593 
    Google Scholar
  • 8b Ishimaru T. Shibata N. Nagai J. Nakamura S. Toru T. Kanemasa S. J. Am. Chem. Soc.  2006,  128:  16488 
    Google Scholar
  • For selected asymmetric ring-expansion reactions, see:
  • 9a Meyers C. Carreira EM. Angew. Chem. Int. Ed.  2003,  42:  694 
    Google Scholar
  • 9b Lerchner A. Carreira EM. J. Am. Chem. Soc.  2002,  124:  14826 
    Google Scholar
  • 9c Alper PB. Meyers C. Lerchner A. Siegel DR. Carreira EM. Angew. Chem. Int. Ed.  1999,  38:  3186 
    Google Scholar
  • For selected asymmetric 1,4- and 1,2-addition reactions, see:
  • 10a Liao Y.-H. Liu X.-L. Wu Z.-J. Cun L.-F. Zhang X.-M. Org. Lett.  2010,  12:  2896 
    Google Scholar
  • 10b Li X. Zhang B. Xi Z.-G. Luo S.-Z. Cheng J.-P. Adv. Synth. Catal.  2010,  352:  416 
    Google Scholar
  • 10c He R.-J. Shirakawa S. Maruoka K.
    J. Am. Chem. Soc.  2009,  131:  16620 
    Google Scholar
  • 10d Bui T. Syed S. Barbas CF. J. Am. Chem. Soc.  2009,  131:  8758 
    Google Scholar
  • 10e Kato Y. Furutachi M. Chen Z. Mitsunuma H. Matsunaga S. Shibasaki M. J. Am. Chem. Soc.  2009,  131:  9168 
    Google Scholar
  • 10f Lai H.-S. Huang Z.-Y. Wu Q. Qin Y. J. Org. Chem.  2009,  74:  283 
    Google Scholar
  • 10g Shintani R. Inoue M. Hayashi T. Angew. Chem. Int. Ed.  2006,  45:  3353 
    Google Scholar
  • 10h Toullec PY. Jagt RBC. de Vries JG. Feringa BL. Minnaard AJ. Org. Lett.  2006,  8:  2715 
    Google Scholar
  • For selected asymmetric cycloaddition reactions, see:
  • 11a Lv H. Chen X.-Y. Sun L.-H. Ye S. J. Org. Chem.  2010,  75:  6973 
    Google Scholar
  • 11b Chen X.-H. Wei Q. Luo S.-W. Xiao H. Gong L.-Z. J. Am. Chem. Soc.  2009,  131:  13819 
    Google Scholar
  • 11c Trost BM. Cramer N. Silverman SM. J. Am. Chem. Soc.  2007,  129:  12396 
    Google Scholar
  • For selected asymmetric Mannich reactions, see:
  • 12a Cheng L. Liu L. Jia H. Wang D. Chen Y.-J. J. Org. Chem.  2009,  74:  4650 
    Google Scholar
  • 12b Tian X. Jiang K. Peng J. Du W. Chen Y.-C. Org. Lett.  2008,  10:  3583 
    Google Scholar
  • For reactions using oxindole motif as electrophiles, see:
  • 13a Pesciaioli F. Righi P. Mazzanti A. Bartoli G. Bencivenni G. Chem. Eur. J.  2011,  17:  2842 
    Google Scholar
  • 13b Bencivenni G. Wu LY. Mazzanti A. Giannichi B. Pesciaioli F. Song MP. Bartoli G. Melchiorre P. Angew. Chem. Int. Ed.  2009,  48:  7200 
    Google Scholar
  • 14a Wang X.-F. Chen J.-R. Cao Y.-J. Cheng H.-G. Xiao W.-J. Org. Lett.  2010,  12:  1140 
    Google Scholar
  • 14b Wang X.-F. Hua Q.-L. Cheng Y. An X.-L. Yang Q.-Q. Chen J.-R. Xiao W.-J. Angew. Chem. Int. Ed.  2010,  49:  8379 
    Google Scholar
  • 14c Zhang F.-G. Yang Q.-Q. Xuan J. Lu H.-H. Duan S.-W. Xiao W.-J. Org. Lett.  2010,  12:  5636 
    Google Scholar
  • 14d Chen J.-R. Cao Y.-J. Zou Y.-Q. Tan F. Fu L. Zhu X.-Y. Xiao W.-J. Org. Biomol. Chem.  2010,  8:  1275 
    Google Scholar
  • 14e Lu H.-H. Wang X.-F. Yao C.-J. Zhang J.-M. Wu H. Xiao W.-J. Chem. Commun.  2009,  4251 
    Google Scholar
  • 14f Lu H.-H. Zhang F.-G. Meng X.-G. Duan S.-W. Xiao W.-J. Org. Lett.  2009,  11:  3946 
    Google Scholar
  • 14g Cao Y.-J. Lai Y.-Y. Wang X. Li Y.-J. Xiao W.-J. Tetrahedron Lett.  2007,  48:  21 
    Google Scholar
  • 14h Cao Y.-J. Lu H.-H. Lai Y.-Y. Lu L.-Q. Xiao W.-J. Synthesis  2006,  3795 
    Google Scholar