PDF icon PDF herunterladen
Synthesis 2011(16): 2664-2670  
DOI: 10.1055/s-0030-1260120
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Stereoselective Route to cis-(2S,3R)-3-Hydroxypipecolic Acid and Two Enantiomeric cis-2-Hydroxymethyl-3-hydroxypiperidine Derivatives

Shital K. Chattopadhyay*, Shankar P. Roy, Tapan Saha
Department of Chemistry, University of Kalyani, Kalyani-741235, West Bengal, India
Fax: +91(33)25828282; e-Mail: skchatto@yahoo.com;
Weitere Informationen

Publikationsverlauf

Received 13 May 2011
Publikationsdatum:
14. Juli 2011 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

Stereoselective routes to cis-(2S,3R)-3-hydroxypipecolic acid and two enantiomeric cis-2-hydroxymethyl-3-hydroxypiperidine derivatives from a common precursor have been developed, which featured stereocontrolled vinylation of a α-chiral aldehyde and ring-closing metathesis as key steps.

Key words

amino acids - diastereoselectivity - piperidines - chiral pool - metathesis

    References

  • 1 Schneider M. Pyridine and Piperidine Alkaloids: An Update, In Alkaloids: Chemical and Biological Perspectives   Vol. 10:  Pelletier SW. Pergamon; Oxford: 1996.  p.155-299  
    Suche in Google Scholar
  • 2a Butters TD. Dwek RA. Platt FM. Chem. Rev.  2000,  100:  4683 
    Suche in Google Scholar
  • 2b Naoki-Asano RJ. Nash RJ. Molyneux G. Fleet GWJ. Tetrahedron: Asymmetry  2000,  11:  1645 
    Suche in Google Scholar
  • For some leading reviews, see:
  • 3a Buffat MGP. Tetrahedron  2004,  60:  1701 
    Suche in Google Scholar
  • 3b Laschat S. Dickner T. Synthesis  2000,  1781 
  • 3c Weintraub PM. Sabol JS. Kane JM. Borcherding DR. Tetrahedron  2003,  59:  2953 
    Suche in Google Scholar
  • 3d Kadouri-Pouchot C. Comesse S. Amino Acids  2005,  29:  101 
    Suche in Google Scholar
  • 4a Suzuki K. Sato T. Morika M. Nagai K. Kenji A. Yamaguchi H. Sato T. J. Antibiot.  1991,  44:  479 
    Suche in Google Scholar
  • 4b Scott JD. Tipple TN. Williams RN. Tetrahedron Lett.  1998,  39:  3659 
    Suche in Google Scholar
  • 5 Ferreira F. Greck C. Genet JP. Bull. Soc. Chim. Fr.  1997,  134:  615 
    Suche in Google Scholar
  • For some leading monograph and references, see:
  • 6a Synthesis of peptides and peptidomimetics: Houben-Weyl Methods in Organic Chemistry   Goodman M. Felix A. Moroder L. Toniolo C. Thieme; Stuttgart: 2001. 
  • 6b Cowell SM. Lee YS. Cain JP. Hruby VJ. Curr. Med. Chem.  2004,  11:  2785 
    Suche in Google Scholar
  • 6c Hanessian S. Mcnaughton-Smith G. Lombart H.-G. Lubell WD. Tetrahedron  1997,  53:  12789 
    Suche in Google Scholar
  • 6d Battistini L. Zanardi F. Rassu G. Spanu P. Pelosi G. Fava GG. Ferrari MB. Casiraghi G. Tetrahedron: Asymmetry  1997,  17:  2975 
    Suche in Google Scholar
  • 6e Copeland TD. Wondrak EM. Toszer J. Roberts MM. Oraszan S. Biochem. Biophys. Res. Commun.  1990,  169:  310 
    Suche in Google Scholar
  • 6f Quibell M. Benn A. Finn N. Monk T. Ramjee M. Wang Y. Watts J. Bioorg. Med. Chem.  2004,  12:  5689 
    Suche in Google Scholar
  • 6g Deska J. Kazmaier U. Chem. Eur. J.  2007,  13:  6204 
    Suche in Google Scholar
  • 7a Enders D. Nolte B. Runsink J. Tetrahedron: Asymmetry  2002,  13:  587 
    Suche in Google Scholar
  • 7b Lillelund VH. Jensen HH. Liang X. Bols M. Chem. Rev.  2002,  102:  515 
    Suche in Google Scholar
  • 7c Meyers AI. Andres CJ. Resek JE. Woodall CC. McLaughlin MA. Lee PH. Price DA. Tetrahedron  1999,  55:  8931 
    Suche in Google Scholar
  • 8a Kuehl FA. Spencer CF. Folkers K. J. Am. Chem. Soc.  1948,  70:  2091 
    Suche in Google Scholar
  • 8b Kobayashi S. Ueno M. Suzuki R. Tetrahedron Lett.  1999,  40:  2175 
    Suche in Google Scholar
  • For synthetic reports on trans-(2S,3S)-3-hydroxypipecolic acid, see:
  • 9a Chavan SP. Dumare NB. Harale KR. Kalkote UR. Tetrahedron Lett.  2011,  52:  404 
    Suche in Google Scholar
  • 9b Lemire A. Charette AB. J. Org. Chem.  2010,  75:  2077 
    Suche in Google Scholar
  • 9c Liu L.-X. Peng Q.-L. Huang P.-Q. Tetrahedron: Asymmetry  2008,  19:  1200 
    Suche in Google Scholar
  • 9d Kim IS. Ji YJ. Jung YH. Tetrahedron Lett.  2006,  47:  7289 
    Suche in Google Scholar
  • 9e Agami C. Couty F. Mathieu H. Tetrahedron Lett.  1996,  37:  4001 
    Suche in Google Scholar
  • For the (2R,3R)-isomer, see:
  • 9f Alegret C. Ginesta X. Riera A. Eur. J. Org. Chem.  2008,  1789 
  • 9g Haddad M. Larcheveque M. Tetrahedron Lett.  2001,  42:  5223 
    Suche in Google Scholar
  • For common approaches to both (2S,3S)- and (2R,3R)-isomers, see:
  • 9h Kumar P. Bodas MS. J. Org. Chem.  2005,  70:  360 
    Suche in Google Scholar
  • 9i Scott JD. Tippie TN. Williams RM. Tetrahedron Lett.  1998,  39:  3659 
    Suche in Google Scholar
  • 9j Battistini L. Zanardi F. Rassu G. Spanu P. Pelosi G. Fava GG. Ferrari MB. Casiraghi G. Tetrahedron: Asymmetry  1997,  8:  2975 
    Suche in Google Scholar
  • 9k Greck C. Ferreira F. Genet JP. Tetrahedron Lett.  1996,  37:  2031 
    Suche in Google Scholar
  • For common approach for the synthesis of cis- and trans-3-hydroxypipecolic acid, see:
  • 10a Cochi A. Burger B. Navarro C. Pardo DG. Cossy J. Zhao Y. Cohen T. Synlett  2009,  2157 
  • 10b Wang B. Liu R.-H. Eur. J. Org. Chem.  2009,  2854 
  • 10c Yoshimura Y. Ohara C. Imahori T. Saito Y. Kato A. Miyauchi S. Adachi I. Takahata H. Bioorg. Med. Chem.  2008,  16:  8273 
    Suche in Google Scholar
  • 10d Kim IS. Oh JS. Zee OP. Jung YH. Tetrahedron  2007,  63:  2622 
    Suche in Google Scholar
  • 10e Liang N. Datta A. J. Org. Chem.  2005,  70:  10182 
    Suche in Google Scholar
  • 10f Jourdant A. Zhu J. Tetrahedron Lett.  2000,  41:  7033 
    Suche in Google Scholar
  • Reports on cis-(2S,3R)-3-hydroxypipecolic acid:
  • 11a Chung HS. Shin WK. Choi SY. Chung YK. Lee E. Tetrahedron Lett.  2010,  51:  707 
    Suche in Google Scholar
  • 11b Kalamkar NB. Kasture VM. Dhavale DD. J. Org. Chem.  2008,  73:  3619 
    Suche in Google Scholar
  • 11c Pham V.-T. Joo J.-E. Tian Y.-S. Chung Y.-S. Lee K.-Y. Oh C.-Y. Ham W.-H. Tetrahedron: Asymmetry  2008,  19:  318 
    Suche in Google Scholar
  • 11d Scott JD. Williams RM. Tetrahedron Lett.  2000,  41:  8413 
    Suche in Google Scholar
  • Synthesis of cis-(2R,3S)-3-hydroxypipecolic acid:
  • 11e Senthil Kumar P. Baskaran S. Tetrahedron Lett.  2009,  50:  3489 
    Suche in Google Scholar
  • 11f Roemmele RC. Rapoport H. J. Org. Chem.  1998,  54:  1866 
    Suche in Google Scholar
  • 11g Knight DW. Lewis N. Share AC. Haigh D. J. Chem. Soc., Perkin Trans. 1  1998,  3673 
  • 12 Chattopadhyay SK. Biswas T. Biswas T. Tetrahedron Lett.  2008,  49:  1365 
    CrossrefSuche in Google Scholar
  • 13a Garner P. Park JM. J. Org. Chem.  1988,  53:  2979 
    Suche in Google Scholar
  • 13b McKillop A. Taylor RJK. Watson R. Lewis N. Synthesis  1994,  31 
  • 14a Denis J.-N. Correa A. Greene AE. J. Org. Chem.  1991,  56:  6939 
    Suche in Google Scholar
  • 14b Ibuka T. Habashita H. Otaka A. Fujii N. Oguchi Y. Uyehara T. Yamamoto Y. J. Org. Chem.  1991,  56:  4370 
    Suche in Google Scholar
  • 14c Sames D. Polt R. J. Org. Chem.  1994,  59:  4596 
    Suche in Google Scholar
  • 14d Ravikumar JS. Dutta A. Tetrahedron Lett.  1999,  40:  1381 
    Suche in Google Scholar
  • 15 For our recent related work, see: Roy SP. Chattopadhyay SK. Tetrahedron Lett.  2008,  49:  5498 
    CrossrefSuche in Google Scholar
  • For some recent reports on piperidine derivatives, see:
  • 16a Davies SG. Hughes DG. Price PD. Roberts PM. Russell AJ. Smith AD. Thomson JE. Williams OMH. Synlett  2010,  567 
  • 16b Bilke JL. Moore SP. O’Brien P. Gilday J. Org. Lett.  2009,  11:  1935 
    Suche in Google Scholar
  • 16c Kalch D. Rycke ND. Moreau X. Greck C. Tetrahedron Lett.  2009,  50:  492 
    Suche in Google Scholar
  • 16d Noe MC. Hawkins JM. Snow SL. Wolf-Gouveia L. J. Org. Chem.  2008,  73:  3295 
    Suche in Google Scholar
  • 16e Sun C.-S. Lin Y.-S. Hou D.-R. J. Org. Chem.  2008,  73:  6877 
    Suche in Google Scholar
  • 16f Rodriguez D. Pico A. Moyano A. Tetrahedron Lett.  2008,  49:  6866 
    Suche in Google Scholar
  • 16g Hekking KFW. Waalboer DCJ. Moelands MAH. van Delft FL. Rutjes FPJT. Adv. Synth. Catal.  2008,  350:  95 
    Suche in Google Scholar
  • 16h Takahata H. Banba Y. Ouchi H. Memoto H. Org. Lett.  2003,  5:  2527 
    Suche in Google Scholar
  • 17a Schwab P. Grubbs RH. Ziller JW. J. Am. Chem. Soc.  1996,  118:  100 
    Suche in Google Scholar
  • For some reviews, see:
  • 17b Chattopadhyay SK. Karmakar S. Biswas T. Majumdar KC. Rahaman H. Roy B. Tetrahedron  2007,  63:  3919 
    Suche in Google Scholar
  • 17c Grubbs RH. Tetrahedron  2004,  60:  2117 
    Suche in Google Scholar
  • 17d Martin SF. Dieters A. Chem. Rev.  2004,  104:  2199 
    Suche in Google Scholar
  • 18 Dess DB. Martin JC. J. Am. Chem. Soc.  1991,  113:  7277 
    CrossrefSuche in Google Scholar
  • 19 Bal BS. Childers WE. Pinnick HW. Tetrahedron  1981,  37:  2091 
    CrossrefSuche in Google Scholar
  • 20 Horikawa M. Busch-Peterson J. Corey EJ. Tetrahedron Lett.  1999,  40:  3843 
    CrossrefSuche in Google Scholar
  • 21a Herold P. Helv. Chim. Acta  1988,  71:  354 
    Suche in Google Scholar
  • 21b Bandyopadhyay A. Pal BK. Chattopadhyay SK. Tetrahedron: Asymmetry  2008,  19:  1875 
    Suche in Google Scholar