156208-22-9

Upstream product

• 103-82-2 phenylacetic acid 
• 65253-04-5 (-)-8-phenylmenthol 

Downstream Products

• 158779-92-1 (-)-8-Phenylmenthyl (R)-2-phenylbutyrate 
• 16460-75-6 (R)-2-phenyl-butan-1-ol 
• 1451218-48-6 (1R,2S,5R)-8-phenylmenthyl (R)-2-(4-bromophenylamino)-2-phenylacetate 
• 1451218-47-5 (1R,2S,5R)-8-phenylmenthyl (R)-2-(4-nitrophenylamino)-2-phenylacetate 
• 1451218-46-4 (1R,2S,5R)-8-phenylmenthyl (R)-2-(p-toluidino)-2-phenylacetate 
• 1451218-50-0 C₃₁H₃₇NO₂ 
• 1451218-45-3 (1R,2S,5R)-8-phenylmenthyl (R)-2-(p-toluidino)-2-phenylacetate 
• 1451218-44-2 (1R,2S,5R)-8-phenylmenthyl (S)-2-(methylphenylamino)-2-phenylacetate 
• 1451218-43-1 (1R,2S,5R)-8-phenylmenthyl (R)-2-(3-chlorophenylamino)-2-phenylacetate 
• 1451218-42-0 (1R,2S,5R)-8-phenylmenthyl (R)-2-(2-chlorophenylamino)-2-phenylacetate 
• 1451218-41-9 (1R,2S,5R)-8-phenylmenthyl (R)-2-(phenylamino)-2-phenylacetate 
• 1451218-49-7 C₃₀H₃₅NO₂ 
• 1451218-38-4 (1R,2S,5R)-8-phenylmenthyl (R)-2-(4-chlorophenylamino)-2-phenylacetate 
• 161634-63-5 (-)-(1R,3R,4S)-8-phenylmenthyl 2-diazo-2-phenylacetate 

Relevant academic research and scientific papers

Stereochemistry of Silyl Ketene Acetals of Some 8-Phenylmenthyl Arylacetates

Trimethylsilyl ketene acetals derived from 8-phenylmenthyl phenyl-, p-fluorophenyl, and p-(trifluoromethyl)phenylacetates, methyl phenylacetate, and isopropyl phenylacetate have been studied.It was shown that it is not possible, under kinetic conditions, to form exclusively the desired E-isomer and that the thermodynamic Z-isomer is also obtained as the major product under reaction conditions which can be considered kinetic.The results could be rationalized using the Ireland's and Dauben's models on the basis of the changes in the acidity of the proton to be abstraced and the strength of the base.Dimethyl-tert-butylsilyl ketene acetals have been studied.It appeared that reaction of TBDMSCl onto the Li-enolates favored the E-isomer.We proposed that, at the temperature (above -20 deg C) at which the reaction occurs, the E-Z equilibrium between the Li-enolates starts to play a role, and therefore the silyl ketene acetals E/Z ratios are kinetically controlled but by the second step (reaction of the reagent onto the Li-enolate).

Acetone cyanohydrin as a source of HCN in the Cu-catalyzed hydrocyanation of α-aryl diazoacetates

A procedure for the Cu-catalyzed hydrocyanation of α-aryl diazoesters has been developed using acetone cyanohydrin as a source of hydrogen cyanide (HCN). It was found that the addition of trimethylsilyl cyanide (TMSCN) significantly accelerates the conversion presumably by delivering free cyanide ion in situ, thus producing various types of α-aryl cyanoacetates in high yields under mild conditions.

Diastereoselective Alkylation of 8-Phenylmenthyl Phenylacetate: Aggregated Lithium Enolate versus "Naked" Enolate

It is shown that monoalkylation of 8-phenylmenthyl phenylacetate using lithiated bases leads to poor or no diastereoselectivities (50/50 to 69/31) and high yields (75 to 98percent) while alkylation using tBu-P4 (a strong and cation free base, known to provide "naked" anion) leads to high diastereoselectivities (92/8 to 98/2) and high yields (65 to 95percent).It is postulated that, in the case of phenylacetates, the degree of aggregation of the lithium enolate is responsible of the poor diastereoselectivities.