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A New Method for the Preparation of ( E )‐3‐Acylprop‐2‐enoic Acids
Author(s) -
Obrecht Daniel,
Weiss Bettina
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720115
Subject(s) - chemistry , isomerization , mechanism (biology) , combinatorial chemistry , organic chemistry , computational chemistry , stereochemistry , catalysis , philosophy , epistemology
A new method for the preparation of ( E )‐3‐acylprop‐2‐enoic acids ( = ( E )‐3‐acylacrylic acids) of type II via acid‐catalyzed isomerization of the corresponding 3‐acylprop‐2‐ynal acetals of type I ( Scheme 1 ) has been found. The described reaction gives a rapid and quite general access to these compounds known to exhibit a number of interesting biological activities. Some studies toward the elucidation of the reaction mechanism have been made, and a hypothetical mechanism is proposed.