134540-58-2

Upstream product

• 13674-16-3 methyl 2-hydroxy-3-phenylpropanoate 
• 108-24-7 acetic anhydride 
• 828-01-3 phenyllactic acid 
• 50353-47-4 phenyl acetaldehyde cyanohydrin 
• 122-78-1 phenylacetaldehyde 
• 81691-59-0 (2RS,3RS)-2,3-dihydroxy-3-phenyl-propionic acid methyl ester 
• 75-36-5 acetyl chloride 
• 132377-76-5 (2R*,3R*)-methyl 2-acetoxy-3-bromo-3-phenylpropionate 
• 142-71-2 copper diacetate 
• 51507-18-7 methyl 2-diazohydrocinnamate 

Relevant academic research and scientific papers

Oxidation of α-acetoxy acetals with trichloroisocyanuric acid

α-Acetoxy acid methyl esters are prepared in excellent yields by treating aliphatic α-acetoxy dimethyl acetals with trichloroisocyanuric acid in DMF.

Synthesis of α-diazoesters from α-hydrazonoesters: Utilization of α-hydrazonoesters and α-diazoesters for convenient interconversion

We have developed a novel method to synthesize α-diazoesters from α-hydrazonoesters with a catalytic amount of Cu(OAc)2 in acetonitrile. When the reaction was carried out under an argon atmosphere, the reaction stopped halfway, suggesting that this reaction required oxygen to reoxidize the catalyst. Since hydrazonoesters can be obtained by reduction of α-diazoesters with P(n-Bu)3 in diisopropyl ether, these 2 compounds are mutually interconvertible with ease. Whereas α-diazoesters are unstable and unsuitable for storage, hydrazonoesters are more stable, especially crystalline hydrazonoesters. Thus, hydrazonoesters, which are suitable for long-term storage, could be conveniently used as precursors for α-diazoesters.

Kinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Selective Transformations of threo-2,3-Dihydroxy Esters

Two highly regio- and stereoselective transformations of threo-2,3-dihydroxy esters have been developed.In the first reaction, the α-hydroxy group is converted into a sulfonate group (tosylate or nosylate); the α-tosylates and α-nosylates are then subjected to basic conditions (K2CO3/ROH) to give erythro glycidic esters in high yield.The α-nosylates are also suitable electrophiles for azides, giving access to erythro-α-azido-β-hydroxy esters.The second reaction involves conversion of the diol esters to acetoxy bromo esters.The β-subsituent plays a key role in determining the regiochemistry since cases with β-alkyl substituents afford β-acetoxy-α-bromo esters exclusively, whereas a β-phenyl substitutent directs formation of the α-acetoxy-β-bromo ester.The acetoxy bromo esters can subsequently be converted to the threo glycidic esters (via the bromohydrin esters); selective hydrogenolysis of the bromine substituent can also be achieved.