255914-99-9Relevant academic research and scientific papers
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 (1994)
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
Stereocontrol in the reduction of meso-imides using oxazaborolidine, leading to a facile synthesis of (+)-deoxybiotin
Shimizu, Makoto,Nishigaki, Yoshimasa,Wakabayashi, Akinobu
, p. 8873 - 8876 (2007/10/03)
Highly enantioselective reduction of meso-imides was conducted using oxazaborolidine derived from L-threonine and borane-THF complex to give lactams in high enantiomeric purity. This methodology was successfully applied to the synthesis of (+)-deoxybiotin
Enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides and 1,2-dicarboximides: Asymmetric synthesis of bicyclic lactones and hydroxylactams
Matsuki,Inoue,Ishida,Takeda,Nakagawa,Hino
, p. 9 - 18 (2007/10/02)
Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2- dicarboxylic anhydrides (1, 4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2- naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.
