203263-75-6

Upstream product

• 83402-87-3 2-oxo-4-phenylbutyric acid methyl ester 
• 108-93-0 cyclohexanol 
• 710-11-2 2-oxo-4-phenylbutyric acid 
• 64920-29-2 2-oxo-4-phenylbutanoic acid ethyl ester 
• 103-63-9 1-phenyl-2-bromoethane 

Relevant academic research and scientific papers

Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates

Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.

Stereochemical Control in Microbial Reduction. 30. Reduction of Alkyl 2-Oxo-4-phenylbutyrate as Precursors of Angiotensin Converting Enzyme (ACE) Inhibitors

Alkyl 2-oxo-4-phenylbutyrates are reduced to the corresponding alkyl (R)-2-hydroxy-4-phenylbutyrates, versatile chiral building blocks in organic synthesis, in high chemical yield (80-90%) with excellent stereoselectivity (>90%ee). The reaction has been run in aqueous diethyl ether at 30 °C for 24 h under the catalysis of bakers' yeast (Saccharomyces cerevisiae) which was preincubated for 6 h in the presence of phenacyl chloride. The amount of water in the medium should be controlled strictly not to exceed 0.8 mL (g yeast)-1.