Download PDF
Synlett 2009(17): 2801-2802  
DOI: 10.1055/s-0029-1217983
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Practical Synthesis of (S)-Cyclopent-2-enol

Monica G. Gonçalves-Martin, Andreas Saxer, Philippe Renaud*
Departement für Chemie und Biochemie, Universität Bern, Freiestr. 3, 3012 Bern, Switzerland
Fax: +41(31)6313426; e-Mail: philippe.renaud@ioc.unibe.ch;
Further Information

Publication History

Received 20 July 2009
Publication Date:
24 September 2009 (online)

    Permissions and Reprints All articles of this category

Corrected by:

A Practical Synthesis of (S)-Cyclopent-2-enolSynlett 2010; 2010(05): 840-840
DOI: 10.1055/s-0029-1219555

Abstract

An efficient and scalable procedure for the synthesis of (S)-cyclopent-2-enol is reported. The two key steps of the synthesis are the Noyori’s Ru-catalyzed transfer hydrogenation of an ynone and ring-closing metathesis of a 1,6-heptadiene.

Key words

asymmetric synthesis - transfer hydrogenation - ring-closing metathesis - allylic alcohol

    References

  • 1a Hildbrand S. Troxler T. Scheffold R. Helv. Chim. Acta  1994,  77:  1236 
    Google Scholar
  • 1b Donohoe TJ. Moore PR. Waring MJ. Tetrahedron Lett.  1997,  38:  5027 
    Google Scholar
  • 1c Goering BK. Ganem B. Tetrahedron Lett.  1994,  35:  6997 
    Google Scholar
  • 2 Hu QY. Rege PD. Corey EJ. J. Am. Chem. Soc.  2004,  126:  5984 
    CrossrefGoogle Scholar
  • 3 Schinzer D. Bärmann H. Angew. Chem. Int. Ed.  1996,  35:  1678 
    Google Scholar
  • 4a Huang L. Xue Z. The Alkaloids   Vol. 23:  Academic Press; New York: 1984. 
    Google Scholar
  • 4b Jalil Miah MA. Hudlicky T. Reed JW. The Alkaloids   Vol. 51:  Academic Press; New York: 1998. 
    Google Scholar
  • 5 Gonçalves-Martin MG. Ph.D. Thesis   Universität Bern; Switzerland: 2007. 
    Google Scholar
  • 6a Wahhab A. Tavares DF. Rauk A. Can. J. Chem.  1990,  68:  1559 
    Google Scholar
  • 6b Levina A. Muzart J. Tetrahedron: Asymmetry  1995,  6:  147 
    Google Scholar
  • 6c Kitamura M. Kasahara I. Manabe K. Noyori R. Takaya H. J. Org. Chem.  1988,  53:  708 
    Google Scholar
  • 6d Ito S. Kasai M. Ziffer H. Silverton JV. Can. J. Chem.  1987,  65:  574 
    Google Scholar
  • 6e Hayashi T. Okamoto Y. Kabeta K. Hagihara T. Kumada M. J. Org. Chem.  1984,  49:  4224 
    Google Scholar
  • 6f Gupta AK. Kazlauskas RJ. Tetrahedron: Asymmetry  1993,  4:  879 
    Google Scholar
  • 7a Su H. Walder L. Zhang ZD. Scheffold R. Helv. Chim. Acta  1988,  71:  1073 
    Google Scholar
  • 7b Bonhôte P. Scheffold R. Helv. Chim. Acta  1991,  74:  1425 
    Google Scholar
  • 8 Bertilsson SK. Soedergren MJ. Andersson PG. J. Org. Chem.  2002,  67:  1567 
    CrossrefGoogle Scholar
  • 9a Gais H.-J. Bondarev O. Hetzer R. Tetrahedron Lett.  2005,  46:  6279 
    Google Scholar
  • 9b Lüssem BJ. Gais H.-J. J. Am. Chem. Soc.  2003,  125:  6066 
    Google Scholar
  • 9c Lüssem BJ. Gais H.-J. J. Org. Chem.  2004,  69:  4041 
    Google Scholar
  • 10 Fukazawa T. Hashimoto T. Tetrahedron: Asymmetry  1993,  4:  2323 
    CrossrefGoogle Scholar
  • 11a Gokhale AS. Minidis ABE. Pfaltz A. Tetrahedron Lett.  1995,  36:  1831 
    Google Scholar
  • 11b Andrus MB. Zhou Z. J. Am. Chem. Soc.  2002,  124:  8806 
    Google Scholar
  • 11c Kawasaki K. Tsumura S. Katsuki T. Synlett  1995,  1245 
    Google Scholar
  • 12 Matsumura K. Hashiguchi S. Ikariya T. Noyori R. J. Am. Chem. Soc.  1997,  119:  8738 
    CrossrefGoogle Scholar
  • 13 Kingsbury JS. Harrity JPA. Bonitatebus PJ. Hoveyda AH. J. Am. Chem. Soc.  1999,  121:  791 
    Google Scholar
  • 14a Schwab P. France MB. Ziller JW. Grubbs RH. Angew. Chem. Int. Ed.  1995,  34:  2039 
    Google Scholar
  • 14b Schwab P. Grubbs RH. Ziller JW. J. Am. Chem. Soc.  1996,  118:  100 
    Google Scholar
  • 15 Saturnin C. Tabacchi R. Saxer A. Chimia  1993,  47:  221 
    Google Scholar