Stereochemistry of the asymmetric 1,4-hydride reduction of N-substituted derivatives of ?9,10-octahydro-4-quinolone

Abstract

It is shown that the reaction of LiAlH4 with Δ9, 10-ocathydro-4-quinolones that have chiral (S)-sec-butyl and (S)-α-benzylethyl substituants at the nitrogen atom proceeds as asymmetric 1,4-hydride reduction with the primary formation of trans isomers of (1S)-sec-butyl(9S,10S)- and (1S)-α-benzylethyl(9S,10S)-decahydro-4-quinolones, the three-dimensional structures and absolute configurations of which were established by 13C NMR spectroscopy and circular dichroism measurements.