328575-51-5

Upstream product

• 4412-96-8 3-methylfuran-2-carboxylic acid 
• 22601-06-5 3-methylfuran-2-carbonyl chloride 

Downstream Products

• 462118-92-9 (2R)-2-isobutyl-3-oxo-3,6-dihydro-2H-pyran-2-carboxylic acid 2',6'-dimethylphenyl ester 
• 462118-90-7 (2R)-2-isobutyl-3-methyl-2,5-dihydro-furan-2-carboxylic acid 2',6'-dimethyl-phenyl ester 
• 462118-91-8 (2R)-2-methyl-3-oxo-3,6-dihydro-2H-pyran-2-carboxylic acid 2',6'-dimethyl-phenyl ester 
• 462118-89-4 (2R)-2,3-dimethyl-2,5-dihydrofuran-2-carboxylic acid 2',6'-dimethyl-phenyl ester 

Relevant academic research and scientific papers

Synthesis of Enantiopure Dihydropyranones: Aldol-Based Ring Expansion of Dihydrofurans

(Matrix Presented) The stereoselective Birch reduction of 3-methyl-2-furoic acids using a readily available chiral auxilairy is described; by coupling this process to an oxidative cleavage/aldol ring closure sequence we were able to produce highly functio

Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia

A series of chiral auxiliaries have been attached to 2-furoic acid and 3-methyl-2-furoic acid. The performance of these auxiliaries in the Birch reduction was assessed and it was found that placing a C-3 methyl group on the heterocycle was essential for good stereoselectivity. Using bis(methoxymethyl)pyrrolidine high levels of diastereoselectivity could be obtained with a range of electrophiles. A model is also presented which explains the sense of stereoselectivity displayed by this auxiliary. After reduction, the auxiliaries could be removed by reaction with acid to furnish dihydrofuran-based carboxylic acids with high enantiomeric excess. The Royal Society of Chemistry 2000.