Synthesis 2005(4): 605-609  
DOI: 10.1055/s-2004-837303
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Synthetic Approach to α-Chlorocinnamaldehydes

Valentine G. Nenajdenko*a, Alexander L. Reznichenkoa, Olesya N. Lenkovaa, Alexey V. Shastinb, Elizabeth S. Balenkovaa
a Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russia
b Institute of Problems of Chemical Physics, Chernogolovka, Moscow region, 142432, Russia
Fax: +7(095)9328846; e-Mail: nen@acylium.chem.msu.ru ;
Further Information

Publication History

Received 20 October 2004
Publication Date:
22 December 2004 (eFirst)

Abstract

A new simple and efficient transformation of aromatic aldehydes into α-chlorocinnamaldehydes is described. Catalytic olefination reaction of hydrazones of aromatic aldehydes with 2-trichloromethyl-1,3-dioxolane gives ethylene acetals of target alkenes in moderate to good yields. The reaction proceeds stereoselectively to form preferably Z-isomers.

    References

  • 1a Kelly SE. In Comprehensive Organic Synthesis   Vol. 1:  Trost BM. Fleming I. Pergamon; New York: 1999. 
  • 1b Modern Carbonyl Olefination   Takeda T. Wiley; Weinheim: 2004. 
  • 1c Korotchenko VN. Nenajdenko VG. Balenkova ES. Shastin AV. Russ. Chem. Rev. (Russ. Transl.)  2004,  73:  1039 
  • 2 Tago K. Kogen H. Tetrahedron  2000,  56:  8825 
  • 3 Nenajdenko VG. Korotchenko VN. Shastin AV. Balenkova ES. Russ. Chem. Bull.  2004,  53:  1034 
  • 4a Shastin AV. Korotchenko VN. Nenajdenko VG. Balenkova ES. Tetrahedron  2000,  56:  6557 
  • 4b Shastin AV. Korotchenko VN. Nenajdenko VG. Balenkova ES. Russ. Chem. Bull.  2001,  50:  1401 
  • 4c Korotchenko VN. Shastin AV. Nenajdenko VG. Balenkova ES. Tetrahedron  2001,  57:  7519 
  • 4d Shastin AV. Korotchenko VN. Nenajdenko VG. Balenkova ES. Synthesis  2001,  2081 
  • 4e Korotchenko VN. Shastin AV. Nenajdenko VG. Balenkova ES. J. Chem. Soc., Perkin Trans. 1  2002,  883 
  • 4f Nenajdenko VG. Shastin AV. Korotchenko VN. Varseev GN. Balenkova ES. Eur. J. Org. Chem.  2003,  302 
  • 4g Nenajdenko VG. Shastin AV. Golubinskii IV. Lenkova ON. Balenkova ES. Russ. Chem. Bull.  2004,  53:  228 
  • 4h Nenajdenko VG. Lenkova ON. Shastin AV. Balenkova ES. Synthesis  2004,  573 
  • 5 Rulev AYu. Russ. Chem. Rev. (Russ. Transl.)  1998,  67:  317 
  • 6 Maerkl G. Chem. Ber.  1962,  95:  3003 
  • 7 Dieter R. Nice L. Velu S. Tetrahedron Lett.  1996,  37:  2377 
  • 8 Masure D. Chuit C. Sauvêtre R. Normant JF. Synthesis  1978,  458 
  • 9a Kamigata N. Satoh T. Yoshida M. Bull. Chem. Soc. Jpn.  1988,  61:  449 
  • 9b Ley SV. Whittle AJ. Tetrahedron Lett.  1981,  3301 
  • 10 Satoh T. Kitoh Y. Onda K. Takano K. Yamakawa K. Tetrahedron  1994,  50:  4957 
  • 11 McElvain S. Curry M. J. Am. Chem. Soc.  1948,  70:  3781