174195-98-3

Upstream product

• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 23708-47-6 1,4-bis(bromomagnesium)butane 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 135097-23-3 (2S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 147-85-3 L-proline 
• 77581-28-3 (S)-proline-N-ethyl carbamate methyl ester 
• 185246-67-7 (S)-1-(2-N-ethoxycarbonylpyrrolidinyl)cyclopentanol 

Relevant academic research and scientific papers

COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS

The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

Enantioselective reduction of aromatic ketones catalysed by chiral ruthenium(II) complexes

The catalytic enantioselective reduction of aromatic ketones in 2- propanol is carried out by using ruthenium(II) complexes prepared from [Ru(p- cymene)Cl2]2 and a variety of chiral diamines and β-aminoalcohols derived from α-amino acids. Good conversions (>99%) and enantioselectivities (=96%) are observed under mild reaction conditions. (C) 2000 Elsevier Science Ltd.

Enantioselective reduction of ketones with borane catalyzed by cyclic β-amino alcohols prepared from proline

New catalysts have been prepared from (S)- and (R)-proline and the asymmetric borane reduction of prochiral ketones using these catalysts has been studied. The secondary alcohols were obtained in 76-95% yield with 57-96% enantiomeric excesses.

Intramolecular vs. intermolecular induction in the diastereoselective catalytic reduction of enantiomerically pure ketones with borane in the presence of cyclic β-amino alcohols

Asymmetric reduction of various enantiomerically pure ketones was carried out by using oxazaborolidine catalysts with a variety of achiral and chiral ligands. The efficiency of chiral 1,2-amino alcohols as well as the effect of the stereogenic centers in the substrate on the catalytic asymmetric reduction were studied. It was found that the corresponding secondary alcohols were obtained with extremely high stereoselectivities with the proper choice of chiral ligands although a considerably large double asymmetric induction was observed in some cases.