101776-03-8Relevant articles and documents
Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides
Ostendorf, Martin,Romagnoli, Romeo,Pereiro, Isabel Cabeza,Roos, Eric C.,Moolenaar, Marinus J.,Speckamp, W. Nico,Hiemstra, Henk
, p. 1773 - 1789 (2007/10/03)
Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-α,α-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity.
