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.
Y. Sato and K. Hitomi, J. Chem. Soc., Chem. Commun., 1983, 170 DOI: 10.1039/C39830000170
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