106942-31-8

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 108-94-1 cyclohexanone 
• 5396-14-5 ethyl 2-oxo-2-(2-oxocyclohexyl)acetate 
• 750596-77-1 cyclohex-1-enyl-carbamic acid benzyl ester 

Downstream Products

• 53585-93-6 (R)-(-)-hexahydromandelic acid 
• 106975-25-1 ethyl (R)-2-hydroxy-2-cyclohexylacetate 

Relevant academic research and scientific papers

A FACILE SYNTHESIS OF (R)-(-)-HEXAHYDROMANDELIC ACID WITH FERMENTING BAKER'S YEAST

Optically pure (R)-(-)-hexahydromandelic acid has been prepared stereoselectively in two steps by the asymmetric reduction of ethyl α,2-dioxocyclohexaneacetate with fermenting baker's yeast followed by Clemmensen reduction.

Glyoxylic acid versus ethyl glyoxylate for the aqueous enantio selective Synthesis of α-hydroxy-γ-keto acids and esters by the N-Tosyl-(S a)-binam-l-prolinamide-organocatalyzed aldol reaction

N-Tosyl-(S a)-binam-l-prolinamide is an efficient catalyst for the aqueous aldol reaction between ketones and glyoxylic acid, as the monohydrate or as an aqueous solution, or a 50% toluene solution of ethyl glyoxylate. These reactions led to the formation of chiral α-hydroxy-γ-keto carboxylic acids and esters in high levels of diastereo- and enantioselectivities (up to 97% ee), providing mainly anti aldol products. Only cyclopentanone and cyclohexane-1,4-dione afforded an almost 1:1 mixture of the syn/anti-diastereoisomers; however, the reaction between 4-phenylcyclohexanone and ethyl glyoxylate gave the corresponding syn,syn-product as the major diastereoisomer.

Pyrimidine-derived prolinamides as recoverable bifunctional organocatalysts for enantioselective inter- and intramolecular aldol reactions under solvent-free conditions

Chiral L-prolinamides 2 containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are synthesized and used as general organocatalysts for intermolecular and intramolecular aldol reactions with 1,6-hexanedioic acid as a co-catalyst under solvent-free conditions. The intermolecular reaction between ketone-aldehyde and aldehyde-aldehyde must be performed under wet conditions with catalyst (S,S)-2b at 10 °C, which affords anti-aldols with high regio-, diastereo-, and enantioselectivities. For the Hajos-Parrish-Eder-Sauer-Wiechert reaction, both diastereomers of catalyst 2 give similar results at room temperature in the absence of water to give the corresponding Wieland-Miescher ketone and derivatives. Both types of reactions were scaled up to 1 g, and the organocatalysts were recovered by extractive workup and reused without any appreciable loss in activity. DFT calculations support the stereochemical results of the intermolecular process and the bifunctional role played by the organocatalyst by providing a computational comparison of the H-bonding networks occurring with catalysts 2a and 2b. The intermolecular ketone-aldehyde and aldehyde-aldehyde aldol reactions and the Hajos-Parrish-Eder-Sauer-Wiechert versions with the employment of chiral L-prolinamides containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are successfully performed under solvent-free conditions; WMK = Wieland-Miescher ketone.

Chitosan aerogel beads as a heterogeneous organocatalyst for the asymmetric aldol reaction in the presence of water: An assessment of the effect of additives

The catalytic properties of chitosan aerogel for the direct asymmetric aldol reaction in water assisted by various surfactants and acid co-catalysts have been evaluated by employing a range of donor and acceptor systems. A beneficial effect on both the yi

Organocatalytic enantioselective synthesis of secondary α-hydroxycarboxylates

Enantioenriched secondary α-hydroxycarboxylates have been synthesized in good yields and enantioselectivities by using the cross-aldol reaction of ketones and ethyl glyoxylate with a proline-derived dipeptide as the catalyst. Georg Thieme Verlag Stuttgart

Highly diastereo- and enantioselective reactions of enecarbamates with ethyl glyoxylate to give optically active syn and anti α-alkyl-β- hydroxy imines and ketones

The remarkably selective addition of enecarbamates 2 to ethyl glyoxylate (1) in the presence of a copper-dilmine catalyst (0.1 mol%) gives the corresponding imines 3 in high yields with excellent enantioselectivities. A concerted aza-enetype reaction mech

Highly diastereo- and enantioselective reactions of enecarbamates with an aldehyde

Catalytic asymmetric addition reactions of enecarbamates with ethyl glyoxylate have been developed using CuClO4·4CH3CN and a diimine ligand as the catalyst. Highly diastereo- and enantioselective addition reactions of α-mono-substitu