Stereoselective synthesis of (E)-2-(1-hydroxyalkyl)alk-2-enenitriles via(Z)-1-cyanoalk-1-enyl anion intermediates

1 January 1983

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications

No. 4,p. 170-171
https://doi.org/10.1039/c39830000170

Abstract

Fluoride ion-induced desilylation of (E)-2-trimethylsilylalk-2-enenitriles affords(Z)-1-cyanoalk-1-enyl anion intermediates, which are trapped by carbonyl compounds to give (E)-2-(1-hydroxyalkyl)alk-2-enenitriles with 100% retention of the configuration.

Keywords

HYDROXYALKYL
ENENITRILES
STEREOSELECTIVE
FLUORIDE
DESILYLATION
TRAPPED
GIVE
TRIMETHYLSILYLALK
RETENTION

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