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Synlett 2010(11): 1609-1616  
DOI: 10.1055/s-0029-1258085
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Rapid Synthesis of 2-Aryl Polyhydroxylated Pyrrolidines

Jia-Kun Sua,b, Yue-Mei Jiaa, Ruirui Hec, Pei-Xin Ruia, Nanyin Hanc, Xihui Hec, Junfeng Xianga, Xin Chenc, Jinghua Zhuc, Chu-Yi Yu*a
a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
Fax: +86(10)82616433; e-Mail: yucy@iccas.ac.cn;
b Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
c School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China
Further Information

Publication History

Received 7 April 2010
Publication Date:
11 June 2010 (online)

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Abstract

Friedel-Crafts-type reaction of electron-rich aromatic compounds with polyhydroxylated cyclic nitrones catalyzed by Brønsted acid afforded 2-aryl polyhydroxylated pyrrolidines in good to excellent yields with high diastereoselectivity under mild conditions.

Key words

2-aryl polyhydroxylated pyrrolidines - iminosugars - Brønsted acid - polyhydroxylated cyclic nitrones - Friedel-Crafts ­reaction

    References and Notes

  • 1a Stütz AE. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond   Wiley-VCH; Weinheim: New York: 1999. 
    Google Scholar
  • 1b Compain P. Martin O. Iminosugars: From Synthesis to Therapeutic Applications   John Wiley and Sons; New York: 2007. 
    Google Scholar
  • 1c Watson AA. Fleet GWJ. Asano N. Molyneux RJ. Nash RJ. Phytochemistry  2001,  56:  265 
    Google Scholar
  • 1d Asano N. Nash RJ. Molyneux RJ. Fleet GWJ. Tetrahedron: Asymmetry  2000,  11:  1645 
    Google Scholar
  • 2a Matkhalikova SF. Malikov VM. Yunusov SY. Khim. Prir. Soedin.  1969,  5:  30 
    Google Scholar
  • 2b Shibano M. Tsukamoto D. Kusano G. Heterocycles  2002,  57:  1539 
    Google Scholar
  • 2c Shibano M. Tsukamoto D. Masuda A. Tanaka Y. Kusano G. Chem. Pharm. Bull.  2001,  49:  1362 
    Google Scholar
  • 2d Ishida S. Okasaka M. Ramos F. Kashiwada Y. Takaishi Y. Kodzhimatov OK. Ashurmetov O. J. Nat. Med.  2008,  62:  236 
    Google Scholar
  • 3a Wang CLJ. Calabrese JC. J. Org. Chem.  1991,  56:  4341 
    Google Scholar
  • 3b Yoda H. Nakajima T. Takabe K. Tetrahedron Lett.  1996,  37:  5531 
    Google Scholar
  • 3c Oliveira DF. Severino EA. Correia CRD. Tetrahedron Lett.  1999,  40:  2083 
    Google Scholar
  • 3d Severino EA. Correia CRD. Org. Lett.  2000,  2:  3039 
    Google Scholar
  • 3e Haddad M. Larcheveque M. Synlett  2003,  274 
    Google Scholar
  • 3f Chandrasekhar S. Jagadeshwar V. Prakash SJ. Tetrahedron Lett.  2005,  46:  3127 
    Google Scholar
  • 3g Chowdhury MA. Reissig HU. Synlett  2006,  2383 
    Google Scholar
  • 3h Chandrasekhar S. Saritha B. Jagadeshwar V. Prakash SJ. Tetrahedron: Asymmetry  2006,  17:  1380 
    Google Scholar
  • 3i Reddy JS. Rao BV.
    J. Org. Chem.  2007,  72:  2224 
    Google Scholar
  • 3j Zhou X. Liu WJ. Ye JL. Huang PQ. Tetrahedron  2007,  63:  6346 
    Google Scholar
  • 3k Ribes C. Falomir E. Carda M. Marco JA. J. Org. Chem.  2008,  73:  7779 
    Google Scholar
  • 3l Goti A. Cicchi S. Mannucci V. Cardona F. Guarna F. Merino P. Tejero T. Org. Lett.  2003,  5:  4235 
    Google Scholar
  • 3m Yu CY. Huang MH. Org. Lett.  2006,  8:  3021 
    Google Scholar
  • 3n Gurjar MK. Borhade RG. Puranik VG. Ramana CV. Tetrahedron Lett.  2006,  47:  6979 
    Google Scholar
  • 3o Merino P. Delso I. Tejero T. Cardona F. Goti A. Synlett  2007,  2651 
    Google Scholar
  • 3p Merino P. Delso I. Tejero T. Cardona F. Marradi M. Faggi E. Parmeggiani C. Goti A. Eur. J. Org. Chem.  2008,  2929 
    Google Scholar
  • 4a Schramm VL. Tyler PC. Curr. Top. Med. Chem.  2003,  3:  525 
    Google Scholar
  • 4b Merino P. Tejero T. Delso I. Curr. Med. Chem.  2008,  15:  954 
    Google Scholar
  • 4c Kini GD. Hennen WJ. Robins RK. J. Org. Chem.  1986,  51:  4436 
    Google Scholar
  • 4d Horenstein BA. Zabinski RF. Schramm VL. Tetrahedron Lett.  1993,  34:  7213 
    Google Scholar
  • 4e Holzapfel CW. Crous R. Heterocycles  1998,  48:  1337 
    Google Scholar
  • 4f Momotake A. Mito J. Yamaguchi K. Togo H. Yokoyama M. J. Org. Chem.  1998,  63:  7207 
    Google Scholar
  • 4g Moreno-Vargas AJ. Carmona AT. Mora F. Vogel P. Robina I. Chem. Commun.  2005,  4949 
    Google Scholar
  • 4h Moreno-Clavijo E. Carmona AT. Vera-Ayoso Y. Moreno-Vargas AJ. Bello C. Vogel P. Robina I. Org. Biomol. Chem.  2009,  7:  1192 
    Google Scholar
  • 4i Robina I. Moreno-Vargas AJ. Fernandez-Bolanos JG. Fuentes J. Demange R. Vogel P. Bioorg. Med. Chem. Lett.  2001,  11:  2555 
    Google Scholar
  • 4j Moreno-Vargas AJ. Demange R. Fuentes J. Robina I. Vogel P. Bioorg. Med. Chem. Lett.  2002,  12:  2335 
    Google Scholar
  • 4k Moreno-Vargas AJ. Robina I. Demange R. Vogel P. Helv. Chim. Acta  2003,  86:  1894 
    Google Scholar
  • 4l Momotake A. Togo H. Yokoyama M. J. Chem. Soc., Perkin Trans. 1  1999,  1193 
    Google Scholar
  • 4m Furneaux RH. Limberg G. Tyler PC. Schramm VL. Tetrahedron  1997,  53:  2915 
    Google Scholar
  • 4n Furneaux RH. Schramm VL. Tyler PC. Bioorg. Med. Chem.  1999,  7:  2599 
    Google Scholar
  • 4o Palmer AM. Jager V. Eur. J. Org. Chem.  2001,  1293 
    Google Scholar
  • 4p Severino EA. Costenaro ER. Garcia ALL. Correia CRD. Org. Lett.  2003,  5:  305 
    Google Scholar
  • 4q Tsou EL. Chen SY. Yang MH. Wang SC. Cheng TRR. Cheng WC. Bioorg. Med. Chem.  2008,  16:  10198 
    Google Scholar
  • 4r Yokoyama M. Ikenogami T. Togo H.
    J. Chem. Soc., Perkin Trans. 1  2000,  2067 
    Google Scholar
  • 4s Evans GB. Furneaux RH. Gainsford GJ. Schramm VL. Tyler PC. Tetrahedron  2000,  56:  3053 
    Google Scholar
  • 5 For review, see: Revuelta J. Cicchi S. Goti A. Brandi A. Synthesis  2007,  485 
    Article in Thieme ConnectGoogle Scholar
  • 6a Pellissier H. Tetrahedron  2007,  63:  3235 
    Google Scholar
  • 6b Brandi A. Cicchi S. Cordero FM. Goti A. Chem. Rev.  2003,  103:  1213 
    Google Scholar
  • 6c Gothelf KV. Jørgensen KA. Chem. Rev.  1998,  98:  863 
    Google Scholar
  • 7a Vilaivan T. Bhanthumnavin W. Sritana-Anant Y. Curr. Org. Chem.  2005,  9:  1315 
    Google Scholar
  • 7b Lombardo M. Trombini C. Synthesis  2000,  759 
    Google Scholar
  • 7c Merino P. Nitrones and Cyclic Analogues, In Science of Synthesis   27:  Padwa A. Thieme; Stuttgart: 2004.  p.511 
    Google Scholar
  • 8 Banerji A. Mukhopadhyay AK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1982,  21:  239 
    Google Scholar
  • 9a Chalaye-Mauger H. Denis JN. Averbuch-Pouchot MT. Vallée Y. Tetrahedron  2000,  56:  791 
    Google Scholar
  • 9b Berini C. Minassian F. Pelloux-Leon N. Vallée Y. Tetrahedron Lett.  2005,  46:  8653 
    Google Scholar
  • 9c Berini C. Minassian F. Pelloux-Leon N. Denis JN. Vallée Y. Philouze C. Org. Biomol. Chem.  2008,  6:  2574 
    Google Scholar
  • 9d Routier J. Calancea M. David M. Vallée Y. Denis JN. Eur. J. Org. Chem.  2008,  5687 
    Google Scholar
  • 9e Denis JN. Mauger H. Vallée Y. Tetrahedron Lett.  1997,  38:  8515 
    Google Scholar
  • 10a Cicchi S. Höld I. Brandi A. J. Org. Chem.  1993,  58:  5274 
    Google Scholar
  • 10b Wang WB. Huang MH. Li YX. Rui PX. Hu XG. Zhang W. Su JK. Zhang ZL. Zhu JS. Xu WH. Xie XQ. Jia YM. Yu CY. Synlett  2010,  488 
    Google Scholar
  • 11a Magnus P. Gallagher T. Brown P. Pappalardo P. Acc. Chem. Res.  1984,  17:  35 
    Google Scholar
  • 11b McDanell R. McLean AEM. Hanley AB. Heaney RK. Fenwick GR. Food Chem. Toxicol.  1988,  26:  59 
    Google Scholar
  • 11c Morales-Rios MS. Suarez-Castillo OR. Nat. Prod. Commun.  2008,  3:  629 
    Google Scholar
  • 11d Frederich M. Tits M. Angenot L. Trans. R. Soc. Trop. Med. Hyg.  2008,  102:  11 
    Google Scholar
12

The crystal structures of 19b and 26 have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 756237 and 756238, respectively.