15732-77-1

Upstream product

• 600-22-6 pyruvic acid methyl ester 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 93-58-3 benzoic acid methyl ester 
• 1015-28-7 dimethyl (2-oxo-2-phenylethyl)phosphonate 
• 71-43-2 benzene 
• 15732-75-9 3-benzoyl-2-methylenepropionic acid 
• 67-56-1 methanol 
• 15121-71-8 (E)-2-methyl-3-benzoylpropenoic acid 
• 186581-53-3 diazomethane 
• 2170-03-8 itaconic acid anhydride 

Downstream Products

• 84143-18-0 (S)-2-Methyl-4-oxo-4-phenylbutanoic acid 
• 84143-17-9 (R)-2-methyl-4-oxo-4-phenylbutanoic acid 
• 15121-71-8 (E)-2-methyl-3-benzoylpropenoic acid 
• 15732-78-2 trans-2-Benzoyl-1-methyl-cyclopropan-⁽¹⁾-methylester 

Relevant academic research and scientific papers

HIGHLY ENANTIOSELECTIVE ACCESS TO CYCLIC BETA-AMINO ACIDS

Disclosed herein is a method of forming a compound of formula I: wherein the substituents are defined in the specification. In particular, the compounds of formula I can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities.

Highly Chemo- And Enantioselective Hydrogenation of 2-Substituted-4-oxo-2-alkenoic Acids

The highly chemo- and enantioselective hydrogenation of (E)-2-substituted-4-oxo-2-alkenoic acids was established for the first time using the Rh/JosiPhos complex, affording a series of chiral α-substituted-γ-keto acids with excellent results (up to 99% yield and >99% ee) and high efficiency (up to 3000 TON). In addition, the importance of this methodology was further demonstrated by a concise and gram-scale synthesis of the anti-inflammatory drug (R)-flobufen.

Lithium 3-Lithio-3-tosylalkanoates: β-Acylvinyl Anion Equivalents of β-Lithiated α,β-Unsaturated Carboxylic Acids

The dilithiation of β-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 deg C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11.They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12.When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoroacetic anhydride and base-promoted elimination α,β-butenolides are obtained.This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci).The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicycloundec-7-ene (DBU) afford α,β- and/or β,γ-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively.The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).