Synthesis 2004(4): 573-577  
DOI: 10.1055/s-2004-815951
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Synthetic Approach to α-Chlorocinnamates: First Example of Synthesis of Functionally Substituted Alkenes Using Catalytic Olefination Reaction

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

Publication History

Received 24 September 2003
Publication Date:
03 February 2004 (online)

Abstract

A new simple and efficient transformation of carbonyl compounds to α-chlorocinnamates is described. Catalytic olefination reaction with ethyl trichloroacetate gives target alkenes in moderate to good yields. The reaction with aromatic aldehydes proceeds stereoselectively to form preferably Z-isomers.