606939-75-7

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 5204-64-8 3-pentenoic acid 
• 64-17-5 ethanol 
• 136962-22-6 2,2-dimethyl-5-phenyl-5-(2-butenyl)-1,3-dioxolan-4-one 

Downstream Products

• 136984-50-4 (S)-2-hydroxy-2-phenyl-4-hexenoic acid 
• 137037-04-8 (R)-ethyl 2-hydroxy-2-phenyl-4-hexenoate 

Relevant academic research and scientific papers

Synthesis of Sterically Hindered α-Hydroxycarbonyls through Radical-Radical Coupling

We describe a synthetic approach to sterically hindered α-hydroxy carbonyl compounds through radical-radical coupling. An organic photoredox catalysis reaction converts an aliphatic carboxylic acid and α-ketocarbonyl to a transient alkyl radical and a persistent ketyl radical, respectively, which couple selectively based on the persistent radical effect. This protocol allows the use of primary, secondary, and tertiary aliphatic carboxylic acids to introduce various alkyl substituents onto ketone moieties of α-ketocarbonyls under mild reaction conditions.

PLE catalyzed hydrolyses of α-substituted α-hydroxy esters: The influence of the substituents

The enzymatic hydrolyses of a variety of α-substituted mandelic and lactic esters using pig liver esterase (PLE) have been investigated. High to moderate enantioselectivity was found for various α-substituted mandelic esters, whereas PLE showed low to no enantioselectivity for α-substituted lactic esters. We observed that the enantioselectivity of PLE depends strongly on the length and nature of the substituent at the α-position. Some sequences for an active site model of PLE are discussed.