Stereoselective synthesis of the four stereoisomers of 4-(N,N- dibenzylamino)-2,2-dimethyl-3-hydroxypentanenitrile

Article abstract of DOI:10.1080/00397919708004183

The title compounds 1(a,b) and 1(c,d) were synthesized by (i) non- chelation controlled sodium borohydride reduction of their corresponding α- N,N-dibenzylaminoketones and (ii) the Aldol-type condensation of optically pure N,N-dibenzylaminoaldehydes with the lithium derivative of isobutyronitrile, respectively. Attempted inversion of configurations of these secondary alcohols using the Moriarty method yielded 4 -chloro-3 -N,N- dibenzylaminonitrile via an aziridinium ion intermediate instead of the expected inverted alcohols.