161634-49-7

Upstream product

• 161634-46-4 (1S,2R,5S)-Menthyl 2-oxophenylacetate tosylhydrazone 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 611-73-4 Benzoylformic acid 

Downstream Products

• 1421231-82-4 C₃₁H₂₉FO₄ 

Relevant academic research and scientific papers

Visible-light-promoted selective: O -alkylation of 2-pyridones with α-aryldiazoacetates

A visible-light-promoted O-H insertion reaction between 2-pyridones and α-aryldiazoacetates has been developed. Upon visible light irradiation, the reaction proceeds smoothly under mild and catalyst-free conditions. A wide scope of 2-pyridones and α-aryldiazoacetates are well tolerated, and various O-alkylated 2-pyridones are obtained with perfect selectivity and good functional group tolerance. A photoinduced radical process is probably responsible for the excellent selectivity. This journal is

Silver-mediated direct trifluoromethoxylation of α-diazo esters: Via the -OCF3 anion

Silver-mediated direct trifluoromethoxylation of α-diazo esters and ketosteroid was disclosed. The reactions of alkyl α-diazo arylacetates with AgOCF3 or CF3SO2OCF3/AgF at -30 to 10 °C under a N2 atmosphere provided α-trifluoromethoxyl arylacetates in up to 90% yield, while alkyl α-diazo vinylacetates reacting with CF3SO2OCF3/AgF or AgOCF3 afforded γ-trifluoromethoxyl α,β-unsaturated esters in up to 94% yield. The α-diazo ketosteroid was also trifluoromethoxylated under the standard reaction conditions. This protocol allows for an effective and convenient access to a large number of synthetic building blocks, which are promising in the development of new functional OCF3-molecules.

Amination of Diazocarbonyl Compounds: N-H Insertion under Metal-Free Conditions

Transition-metal-free intermolecular N-H insertion of α-diazocarbonyl compounds is reported. Among the series of nitrogen sources examined, dibenzenesulfonimide was found to be the choice in terms of the yields and the reaction time. Primary mechanistic e

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%.