STEREOSELECTIVE SYNTHESIS OF THE 4 STEREOISOMERS OF IBENZYLAMINO)-2,2-DIMETHYL-3-HYDROXYPENTANENITRILE

The title compounds 1(a,b) and 1(c,d) were synthesized by (i) non-chel ation controlled sodium borohydride reduction of their corresponding a lpha-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 configuratio ns of these secondary alcohols using the Moriarty method yielded 4-chl oro-3-N,N-dibenzylaminonitrile via an aziridinium ion intermediate ins tead of the expected inverted alcohols.