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

Valentine G. Nenajdenko; Olesya N. Lenkova; Alexey V. Shastin; Elizabeth S. Balenkova

doi:10.1055/s-2004-815951

PAPER

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

Valentine G. Nenajdenko*^a, Olesya N. Lenkova^a, Alexey V. Shastin^b, Elizabeth S. Balenkova^a
^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

Abstract

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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.

Key words

catalytic olefination - α-chlorocinnamates - catalysis - alkenes - ethyl trichloroacetate

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References

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