177532-27-3

Upstream product

• 4355-36-6 (+/-)-2-hydroxymethyl-2-phenyl-butyric acid 
• 24765-56-8 2-ethyl-2-phenylpropane-1,3-diol 
• 88253-95-6 dimethyl 2-ethyl-2-phenylmalonate 
• 2613-89-0 phenylmalonic acid 
• 1636-25-5 (ethyl)phenylmalonic acid 
• 88254-02-8 (R)-2-Ethyl-2-phenyl-malonic acid monomethyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of all-carbon quaternary stereocenters via desymmetrization of 2,2-disubstituted 1,3-propanediols

A novel enantioselective desymmetrization of 2,2-disubstituted 1,3-propanediols has been established to generate all-carbon quaternary stereocenters, which has been implemented with BzCl and Et3N in the presence of Pybox(6)-CuCl2 complex in CH2Cl2 or PhMe at 78°C. While all the cyanide-comprising diols were desymmetrized with superb enantioselectivity (higher than 98% ee), the stereoinduction of the other substrates greatly depends on the size difference between the two substituents at the 2-position. When the size difference becomes larger, the corresponding substrates tend to engender enhanced enantioselectivity (up to 99% ee).

Efficient lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols and meso 1,2-diols using 1-ethoxyvinyl 2-furoate

An efficient lipase-catalyzed desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols was developed using 1-ethoxyvinyl 2-furoate 1b, for which the well-known method using vinyl or isopropenyl acetate has had limited success due to low reactivity and easy racemization of the products through acyl group migration. The reagent 1b is highly reactive and converts various prochiral 1,3-diols to the monoesters having a chiral quaternary carbon center with 82-99% ee. These products were stable against racemization under acidic conditions, and their furoyl groups were compatible with oxidative conditions. Prolonging the reaction time led to the kinetic resolution of the monoesters resulting in an increase of their optical purity. The similar desymmetrization of meso cis-1,2-cycloalkanediols gave the monoesters with 82-97% ee without racemization.

Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (-)- and (+)-aminoglutethimides AG and analogues

From a single chiron (R)-(+)-5, available with high enantiomeric excess (97%) by enzymatic hydrolysis (PLE acetonic powder) of a malonate, were prepared convenient precursors of aminoglutethimides (-)-AG-1 and (+)-AG-1. This versatile method also allows preparation of the b-hydroxy ester (R)-9 and its enantiomer (S)-9 as well as the glutethimides (S)-4 and (R)-4 and other analogues.