Regioselective and stereospecific palladium(0)-catalyzed reactions of 4-chloroacetoxyalk-2-enoic esters with carbon and nitrogen nucleophiles
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 1185-1191
- https://doi.org/10.1039/p19900001185
Abstract
In the presence of a palladium(0) catalyst, treatment of 4-chloroacetoxyalk-2-enoic esters with carbon or nitrogen nucleophiles leads to the regioselective substitution at the 4-position. The reactions of optically active esters, prepared from an optically active phenylsulphinylacetic ester and aldehydes, take place with retention of configuration, and those of (E)- and (Z)-esters are not accompanied by the complete geometrical isomerization. The palladium(0)-catalyzed reactions of these esters are assumed to proceed through unsymmetrical π-allyl complexes.Keywords
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