155397-96-9Relevant academic research and scientific papers
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.
Oxazaborolidine catalyzed enantioselective reductions of cyclic meso-imides
Romagnoli, Romeo,Roos, Eric C.,Hiemstra, Henk,Moolenaar, Marinus J.,Nico Speckamp,Kaptein, Bernard,Schoemaker, Hans E.
, p. 1087 - 1090 (2007/10/02)
A new asymmetric reduction method for meso-imides is reported. Treatment of various imides with a mixture of a chiral oxazaborolidine and BH3 leads to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the correspo
