70432-50-7

Usage

InChI:InChI=1/C9H16O3/c1-3-8(10)6-5-7-9(11)12-4-2/h3-7H2,1-2H3

Upstream product

• 3637-13-6 5-oxoheptanoic acid 
• 64-17-5 ethanol 
• 10444-38-9 ethyl 4-cyanobutyrate 
• 5205-39-0 ethyl glutaroyl chloride 
• 925-90-6 ethylmagnesium bromide 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 38049-10-4 ethyl 5-oxo-6-heptenoate 
• 2969-81-5 Ethyl 4-bromobutyrate 

Downstream Products

• 14203-46-4 4-methyl-cyclohexane-1,3-dione 

Relevant academic research and scientific papers

An efficient method for retro-Claisen-type C-C bond cleavage of diketones with tropylium catalyst

The retro-Claisen reaction is frequently used in organic synthesis to access ester derivatives from 1,3-dicarbonyl precursors. The C-C bond cleavage in this reaction is usually promoted by a number of transition-metal Lewis acid catalysts or organic Br?nsted acids/bases. Herein we report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro-Claisen-type reactions. Using this method, a range of synthetically valuable substances can be accessed via solvolysis of 1,3-dicarbonyl compounds.

Remote ester group leads to efficient kinetic resolution of racemic aliphatic alcohols via asymmetric hydrogenation

A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method provides chiral δ-alkyl-δ-hydroxy esters and δ-alkyl-1,5-diols in good yields with high enantioselectivities even at extremely low catalyst loading (0.001 mol %).

Alcohol dehydrogenase-catalyzed synthesis of enantiomerically pure δ-lactones as versatile intermediates for natural product synthesis

Starting from ethyl 4-bromobutyrate, the chemoenzymatic synthesis of 6-vinyl-tetrahydro-pyran-2-one has been accomplished. A screening of a number of available alcohol dehydrogenases and intense optimization of reaction parameters enabled us to establish an efficient synthesis of either enantiomer of the vinyllactone with excellent enantiomeric excess (>99%). The scope of possible applications of enantiopure vinyllactones has been verified by subjection to cross-metathesis resulting in the total synthesis of the insect pheromone (S)-5-hexadecanolide and the cytotoxic styryllactone goniothalamine as well as derivatives thereof. Copyright