Synthesis of optically active 4-hydroxyalk-2-enenitriles; Reaction of optically active 2-(p-chlorophenylsulfinyl)acetonitrile with aldehydes in the presence of piperidine in acetonitrile

Abstract Reaction of optically active 2-(p-chlorophenylsulfinyl)acetonitrile ((R)- 1a ) with aldehydes, in the presence of piperidine in acetonitrile at r.t., gave optically active 4-hydroxyalk-2-enenitriles in good optical and chemical yields. The absolute configuration of (−)-4-hydroxypent-2-enenitrile, predominantly obtained by the reaction of (R)- 1a with propanal, was determined to be R.