96540-63-5

Upstream product

• 36239-09-5 ethyl chlorocarbonylacetate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 64-17-5 ethanol 
• 623-73-4 diazoacetic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 1071-46-1 hydrogen ethyl malonate 

Downstream Products

• 146743-99-9 cinnamyl ethyl α-diazomalonate 
• 1334532-80-7 (1S,3R,3aS,6aS)-ethyl 4-oxo-1,3-diphenylhexahydrofuro[3,4-c]furan-3a-carboxylate 
• 96540-30-6 1-cinnamyl 3-ethyl 2-diazomalonate 
• 96540-34-0 3-ethoxycarbonyl-4-(1-iodobenzyl)-4,5-dihydrofuran-2(3H)-one 
• 96540-32-8 1-ethoxycarbonyl-3-oxa-2-oxo-6-phenylbicyclo<3.1.0>hexane 
• 96540-42-0 3-carbonyl-4-benzyl-4,5-dihydrofuran-2(3H)-one 
• 96540-38-4 3-ethoxycarbonyl-4-benzyl-4,5-dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Synthetic method of malonate compound

The invention discloses a synthetic method of a malonate compound. The method comprises the following steps: taking 3-halogenated propargyl compound as shown in a formula 1, alcohol as shown in a formula 2 and water as raw materials; placing the raw materials in an air atmosphere and at the room temperature to react under the conditions of a palladium catalyst and alkali to prepare the malonate compound as shown in a formula 3.

Pd-catalyzed carbonylation of diazo compounds at atmospheric pressure: A catalytic approach to ketenes

The carbonylation of carbenes through catalytic cycles is highly desirable due to the importance of ketene-mediated reactions in organic synthesis. In this investigation, a highly efficient and mild catalytic approach toward ketene intermediates has been developed based on Pd-catalyzed carbonylation of diazo compounds with CO. When α-diazocarbonyl compounds or N-tosylhydrazone salts are heated in the presence of a palladium catalyst under atmospheric pressure of CO, ketene intermediates are formed in situ, where they undergo further reactions with various nucleophiles such as alcohols, amines, or imines. The Pd-catalyzed tandem carbonylation-Staudinger cycloaddition gives β-lactam derivatives in good yields with excellent trans diastereoselectivity. The results from DFT calculation on the reaction mechanism suggest that Pd is involved in the [2 + 2] cycloaddition process and affects the diastereoselectivity of the β-lactam products by assisting isomerization of the addition intermediate. On the other hand, the acylketenes generated from the Pd-catalyzed carbonylation of α-diazoketones react with imines in a formal [4 + 2] cycloaddition manner to afford 1,3-dioxin-4-one derivatives. This straightforward carbonylation provides a new approach toward highly efficient catalytic generation of ketene species under mild conditions.

Diastereoselectivity in the formation of bicyclic cyclopropane carboxylic acid lactones

The intramolecular cyclization of malonic acid allylic esters yields bicyclic cyclopropane carboxylic acid lactones in a phase transfer catalysed reaction. The substituents of the allylic moiety and the reaction temperature influence the diastereomeric composition of the products.

Synthesis of 4-Alkyl-2(5H)-furanones

An alternative method for the synthesis of 4-alkyl-2(5H)-furanones is described.Intramolecular carbene addition reaction of α-diazo compounds (4) in the presence of rhodium acetate or copper acetylacetonate furnished the bicyclic compounds (5), which were subjected to cyclopropane ring-opening reaction to give the 4-alkyl-4,5-dihydrofuran-2(3H)-ones (6) regioselectively.These compounds (6) were further converted into 4-alkyl-2(5H)-furanones (14) in several steps.Keywords - carbene; intramolecular addition; butenolide; cyclopropanation; ring-opening reaction