126889-14-3

Upstream product

• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 92486-00-5 3-(2-benzyloxyacetyl)thiazolidine-2-thione 
• 31600-43-8 methyl 2-(benzyloxy)acetate 
• 139400-25-2 (Z)-2-benzyloxy-1-methoxy-1-(trimethylsiloxy)ethene 

Downstream Products

• 181996-65-6 2-Benzyloxy-1-phenyl-propane-1,3-diol 
• 154278-19-0 methyl (2S,3R)-2-(benzyloxy)-3-hydroxy-3-phenylpropanoate 
• 1241849-99-9 C₁₇H₁₆O₄ 

Relevant academic research and scientific papers

Efficient Synthesis of Differentiated syn-1,2-Diol Derivatives by Asymmetric Transfer Hydrogenation-Dynamic Kinetic Resolution of α-Alkoxy-Substituted β-Ketoesters

Asymmetric transfer hydrogenation was applied to a wide range of racemic aryl α-alkoxy-β-ketoesters in the presence of well-defined, commercially available, chiral catalyst RuII-(N-p-toluenesulfonyl-1,2-diphenylethylenediamine) and a 5:2 mixture of formic acid and triethylamine as the hydrogen source. Under these conditions, dynamic kinetic resolution was efficiently promoted to provide the corresponding syn α-alkoxy-β-hydroxyesters derived from substituted aromatic and heteroaromatic aldehydes with a high level of diastereoselectivity (diastereomeric ratio (d.r.)>99:1) and an almost perfect enantioselectivity (enantiomeric excess (ee)>99>). Additionally, after extensive screening of the reaction conditions, the use of RuII- and RhIII-tethered precatalysts extended this process to more-challenging substrates that bore alkenyl-, alkynyl-, and alkyl substituents to provide the corresponding syn α-alkoxy-β-hydroxyesters with excellent enantiocontrol (up to 99‰ee) and good to perfect diastereocontrol (d.r.>99:1). Lastly, the synthetic utility of the present protocol was demonstrated by application to the asymmetric synthesis of chiral ester ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)-propanoate, which is an important pharmacophore in a number of peroxisome proliferator-activated receptor α/γ dual agonist advanced drug candidates used for the treatment of type-II diabetes. RuII-catalyzed asymmetric transfer hydrogenation with dynamic kinetic resolution was successfully applied to a wide variety of racemic α-alkoxy-β-ketoesters derived from substituted aromatic and heteroaromatic benzaldehydes and cinnamaldehydes (see scheme; PMB=p-methoxybenzyl, S/C=substrate/catalyst ratio).

A novel carbocationic species paired with tetrakis(pentafluorophenyl)borate anion in catalytic aldol reaction

The aldol reaction of several aldehydes with silyl enol ethers proceeded smoothly to give the corresponding aldols in good to high yields at -78 °C by using 1.0 mol% of a novel cationic species with tetrakis(pentafluorophenyl)borate anion.

PREPARATION AND REACTION OF NOVEL OXYGEN ESTER ENOLATES, 2, REACTION OF GLYCOLATE WITH ALDEHYDES USING DIALKYLBORYL TRIFLATE

The introduction of an oxygen atom substituent into the α-position of oxygen ester made it possible to generate corresponding boron enolates by the use of dialkylboryl trifluoromethanesulfonate.These novel boron enolates of oxygen ester proceeded aldol re

VERSATILE RELATIVE AND ABSOLUTE STEREOCONTROL IN STANNOUS TRIFLATE MEDIATED ALDOL-TYPE REACTIONS OF 3-(2-BENZYLOXYACETYL)THIAZOLIDINE-2-THIONE

In the stannous triflate mediated aldol-type reactions of 3-(2-benzyloxyacetyl)thiazolidine-2-thione, stereochemical course of the reactions is dramatically altered by the addition of tetramethylethylenediamine as a ligand.High asymmetric induction is also achieved by the addition of chiral diamine derived from L-prolin.