Synthesis 2007(8): 1261-1264  
DOI: 10.1055/s-2007-965969
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Preparation of anti-1,2-Disubstituted Homopropargylic Alcohols by Addition of Allenyl(cyano)cuprates to Aldehydes

Nacira Alouane, Emmanuel Vrancken*, Pierre Mangeney*
Institut Fédératif de Recherche FR 2769, UMR 7611, Université Pierre et Marie Curie, 4 Place Jussieu, 75252, Paris Cedex, France
e-Mail: mangeney@ccr.jussieu.fr;
Further Information

Publication History

Received 1 February 2007
Publication Date:
28 February 2007 (online)

Abstract

The generality of the addition of allenyl(cyano)cuprates to aldehydes to afford anti-1,2-disubstituted homopropargylic alcohols was studied. The reaction is general, regardless of the nature of the cyanocuprate, although with alkyl-substituted derivatives the anti selectivity is dependent upon the nature of the aldehyde.

    References

  • 1a Groth U. Kesenheimer C. Neïdhofer J. Synlett  2006,  1859 
  • 1b Marshall JA. Chobanian HR. Yanik MM. Org. Lett.  2001,  3:  3369 
  • 1c Chemla F. Bernard N. Normant J. Eur. J. Org. Chem.  1999,  2067 ; and references cited therein
  • 2a Yamamoto H. In Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991.  p.81 
  • 2b Marshall JA. Chem. Rev.  2000,  100:  3163 
  • 2c Marshall JA. Gung BW. Grachan ML. In Modern Allene Chemistry   Vol. 1:  Krause N. Hashmi SK. Wiley-VCH; Weinheim: 2004.  Chap. 9. p.493 
  • 3a Bernaud F. Vrancken E. Mangeney P. Org. Lett.  2003,  5:  2567 
  • 3b Vrancken E. Alouane N. Gérard H. Mangeney P. J. Org. Chem.  2007,  72:  in press; DOI: 10.1021/jo062344z 
  • For the synthesis of similar derivatives, see:
  • 4a

    Refs.1a, 1c, and 2.

  • 4b Marshall JA. Eidam P. Schenck EH.
    J. Org. Chem.  2006,  71:  4840 
  • 4c Trost BM. Yand H. Probst GD. J. Am. Chem. Soc.  2004,  126:  48 
  • 4d Poisson JF. Normant JF. J. Am. Chem. Soc.  2001,  123:  4639 
  • 4e Nakagawa T. Kasatkin A. Sato F. Tetrahedron Lett.  1995,  36:  3207 
  • 4f Zweifel G. Hahn G. J. Org. Chem.  1984,  49:  4565 
  • 5 Mercier F. Epsztein R. Holand S. Bull. Soc. Chim. Fr.  1972,  690 
  • 6 Bernaud F. Vrancken E. Mangeney P. Synlett  2004,  1080 
  • 7 Alouane N. Bernaud F. Marrot J. Vrancken E. Mangeney P. Org. Lett.  2005,  7:  5797 
  • 8 Ohmiya H. Yorimitsu H. Oshima K. Org. Lett.  2006,  8:  3093 
  • 9 Bestmann HJ. Zeibig T. Vostrowsky O. Synthesis  1990,  1039