161634-63-5

Upstream product

• 65253-04-5 (-)-8-phenylmenthol 
• 156208-22-9 8-Phenylmenthyl phenylacetate 
• 611-73-4 Benzoylformic acid 
• 161634-48-6 C₃₁H₃₆N₂O₄S 
• 88002-15-7 Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester 

Downstream Products

• 88292-43-7 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-2-hydroxyphenylacetate 
• 139005-51-9 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-2-hydroxyphenylacetate 
• 1011515-80-2 (1R,2S,5R)-8-phenylmenthyl (R)-2-(2,2-dimethylvinyl)-2-formyl-2-phenylacetate 
• 1011515-82-4 (1R,2S,5R)-8-phenylmenthyl (R)-3-cyclohexylidene-2-formyl-2-phenylpropanoate 
• 1011515-84-6 (1R,2S,5R)-8-phenylmenthyl (R)-2-formyl-2-(2-phenylprop-1-enyl)-2-phenylacetate 
• 1011515-54-0 (1R,2S,5R)-8-phenylmenthyl (S)-2-formyl-2-phenyl-2-(4-tolyl)acetate 
• 1011515-76-6 (1R,2S,5R)-8-phenylmenthyl (S)-2-formyl-2-(4-methoxyphenyl)-2-phenylacetate 
• 1011515-74-4 (1R,2S,5R)-8-phenylmenthyl (S)-2-formyl-2-phenyl-2-(2-tolyl)acetate 

Relevant academic research and scientific papers

Palladium-catalyzed carbenoid based N-H bond insertions: Application to the synthesis of chiral α-amino esters

A highly efficient palladium-catalyzed carbenoid based N-H bond insertion has been developed. The α-amino esters were obtained in high isolated yields. Moreover, by choosing a suitable chiral auxiliary, stereoselective Pd-catalyzed N-H insertion has been realized. The chiral α-amino esters were obtained in high yields (up to 91%) and with excellent diastereoselectivities (d.r. > 19:1). The Royal Society of Chemistry.

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.

Diatereoselectivity in the O-H Insertion Reactions of Rhodium Carbenoids Derived from Phenyldiazoacetates of Chiral Alcohols. Preparation of α-Hydroxy and α-Alkoxy Esters

A series of phenyldiazoacetates 3 derived from enantiomerically pure alcohols ((-)-borneol, (+)-menthol, (-)-menthol, (-)-8-phenylmenthol, (-)-trans-2-phenylcyclohexanol, (+)-trans-2-phenyl-cyclohexanol, and (-)-10-(dicyclohexylsulfamoyl)-D-isoborneol) were prepared from the corresponding α-keto esters 1 by way of the tosylhydrazones 2.Rhodium(II)-catalyzed decomposition of the diazoacetates 3 in the presence of water or alcohols resulted in carbenoid O-H insertion reactions to give the corresponding 2-hydroxy- or 2-alkoxyphenylacetates in good yield, but with varying degrees of diastereoselectivity.A range of rhodium(II) and other metal catalysts were investigated, with rhodium(II) acetate and rhodium(II) acetamide giving the best results.The stereochemistry of the major diastereomer was proved in most cases by independent synthesis from a mandelic acid derivative of known configuration.Possible mechanisms are discussed.

Diastereoselectivity in the O-H insertion reactions of rhodium carbenoids derived from phenyldiazoacetates of homochiral alcohols

Rhodium(II) acetate catalysed decomposition of the phenyldiazoacetates 3 in the presence of alcohols (methanol, propan-2-ol, tert-butanol) led to the O-H insertion products 4 - 6 in varying yields; the diastereomeric excess of the product ranged from 5-53%.