Synthesis 2011(12): 1968-1973  
DOI: 10.1055/s-0030-1260464
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Enantioselective Michael Addition of Ketones and an Aldehyde to Nitroalkenes Catalyzed by a Binaphthyl Sulfonimide in Water

Chunhua Luo, Da-Ming Du*
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, P. R. of China
e-Mail: dudm@bit.edu.cn;
Further Information

Publication History

Received 17 March 2011
Publication Date:
13 May 2011 (online)

Abstract

A binaphthyl sulfonimide organocatalyst was used to promote highly enantioselective and diastereoselective Michael addition reactions of ketones to nitroalkenes in water. In most cases, the products were obtained in good yields with excellent enantioselectivities and diastereoselectivities (93-97% ee, up to >99:1 dr). The catalyst could also be used in an asymmetric Michael addition of isobutyraldehyde to nitroalkenes to give the desired products in moderate yields and moderate enantioselectivities (up to 83% ee).

    References

  • 1 Dalko PI. Moisan L. Angew. Chem. Int. Ed.  2004,  43:  5138 
  • For recent reviews on asymmetric Michael additions, see:
  • 2a Berner OM. Tedeschi L. Enders D. Eur. J. Org. Chem.  2002,  1877 
  • 2b Ballini R. Bosica G. Fiorini D. Palmieri A. Petrini M. Chem. Rev.  2005,  105:  933 
  • 2c Mukherjee S. Yang JW. Hoffmann S. List B. Chem. Rev.  2007,  107:  5471 
  • 2d Sulzer-Mosse S. Alexakis A. Chem. Commun.  2007,  3123 
  • For selected examples of asymmetric Michael additions of ketones to nitroalkenes, see:
  • 2e Yang ZG. Liu J. Liu XH. Wang Z. Feng XM. Su ZS. Hu CW. Adv. Synth. Catal.  2008,  350:  2001 
  • 2f Li PH. Wang L. Wang M. Zhang YC. Eur. J. Org. Chem.  2008,  1157 
  • 2g Tan B. Zeng XF. Lu YP. Chua PJ. Zhong GF. Org. Lett.  2009,  11:  1927 
  • 2h Belot S. Quintard A. Krause N. Alexakis A. Adv. Synth. Catal.  2010,  352:  667 
  • 2i Lu AD. Wu RH. Wang YM. Zhou ZH. Wu GP. Fang JX. Tang CC. Eur. J. Org. Chem.  2010,  2057 
  • 2j Lv GH. Jin RH. Mai WP. Gao LX. Tetrahedron: Asymmetry  2008,  19:  2568 
  • 2k Sato A. Yoshida M. Hara S. Chem. Commun.  2008,  6242 
  • For asymmetric Michael reactions in water, see:
  • 3a Luo S. Mi X. Liu S. Xu H. Cheng J.-P. Chem. Commun.  2006,  3687 
  • 3b Zu L. Wang J. Li H. Wang W. Org. Lett.  2006,  8:  3077 
  • 3c Yan Z.-Y. Niu Y.-N. Wei H.-L. Wu L.-Y. Zhao Y.-B. Liang Y.-M. Tetrahedron: Asymmetry  2006,  17:  3288 
  • 3d Cao Y.-J. Lai Y.-Y. Wang X. Li Y.-J. Xiao W.-J. Tetrahedron Lett.  2007,  48:  21 
  • 3e Syu S.-E. Kao T.-T. Lin W. Tetrahedron  2010,  66:  891 
  • 3f Palomo C. Landa A. Mielgo A. Oiarbide M. Puente A. Vera S. Angew. Chem. Int. Ed.  2007,  46:  8431 
  • 3g Zhu S. Yu S. Ma D. Angew. Chem. Int. Ed.  2008,  47:  545 
  • 3h Alza E. Cambeiro XC. Jimeno C. Pericàs MA. Org. Lett.  2007,  9:  3717 
  • For asymmetric Michael reactions in brine, see:
  • 4a Mase N. Watanabe K. Yoda H. Takabe K. Tanaka F. Barbas CF. J. Am. Chem. Soc.  2006,  128:  4966 
  • 4b Vishnumaya Singh VK. Org. Lett.  2007,  9:  1117 
  • 4c Wu J. Ni B. Headley AD. Org. Lett.  2009,  11:  3354 
  • 5 For asymmetric Michael reactions in ionic liquids, see: Luo S. Mi X. Zhang L. Liu S. Xu H. Cheng J.-P. Angew. Chem. Int. Ed.  2006,  45:  3093 
  • 6 Li CJ. Chem. Rev.  2005,  105:  3095 
  • 7 Ban SR. Du D.-M. Liu H. Yang W. Eur. J. Org. Chem.  2010,  5160 
  • 8 He T. Gu Q. Wu XY. Tetrahedron  2010,  66:  3195