112423-41-3

Upstream product

• 5703-57-1 3-phenylpent-4-enoic acid 
• 51212-29-4 β-formylbenzenepropanoic acid methyl ester 
• 2747-38-8 methyltrichlorotitanium 
• 917-54-4 methyllithium 
• 75-07-0 acetaldehyde 
• 4192-77-2 ethyl cinnamate 
• 123-63-7 paracetaldehyde 
• 2678-54-8 ketene diethyl acetal 
• 67279-69-0 cis-4,5-dihydro-5-iodomethyl-4-phenyl-2(3H)-furanone 
• 6049-50-9 4-Oxo-3-phenylpentanoic acid 

Relevant academic research and scientific papers

Europium-Catalyzed Intramolecular Addition of Carboxylic Acid to Nonactivated Alkenes: An Efficient Route to Aryl-Substituted γ-Butyrolactone

Europium(III)triflate has been proved to be an effective catalyst for intramolecular cyclization of aryl-substituted carboxylic acid to afford arylated γ-butyrolactone. Various attractive features, such as broad substrate scope, a wide range of functional

Lactones 30. Reaction of halolactones with trialkylphosphites

The reaction of halolactones with trialkylphosphites in the presence of water afforded dehalogenated lactones.

(HMe 2 SiCH 2) 2: A Useful Reagent for B(C 6 F 5) 3 -Catalyzed Reduction-Lactonization of Keto Acids: Concise Syntheses of (-)- cis -Whisky and (-)- cis -Cognac Lactones

(HMe 2 SiCH 2) 2 has been utilized as a useful reagent for B(C 6 F 5) 3 -catalyzed reduction-lactonization of keto acids to synthesize γ- and δ-lactones. The process led concisely to (-)- cis -whisky and (-)- cis -cognac lactones in respective overall yields of 32% and 36%.

Copper-catalysed intramolecular O-H addition to unactivated alkenes

Intramolecular cyclisation of ω-alkenoic acids and alkenols can be achieved using a catalytic amount of Cu(OTf)2 to afford lactones and cyclic ethers, offering a practical alternative to existing catalysts.

Intramolecular additions of alcohols and carboxylic acids to inert olefins catalyzed by silver(I) triflate

(Chemical Equation Presented) Intramolecular additions of hydroxyl or carboxyl groups to inert olefins catalyzed by simple silver(I) triflate are described. Good to excellent yields can be obtained for a range of substrates under relatively mild conditions. This reaction represents one of the simplest methods to construct cyclic ethers or lactones.

Ester Groups as Effective Ligands in Chelate-Controlled Additions of Cuprates and Grignard Reagents to Chiral β-Formyl Esters

Addition of cuprates to chiral methyl β-formyl carboxylates 1a-1d provided γ-lactones 2-7 in excellent trans-selectivity.The high diastereofacial selectivity was only obtained employing diethyl ether as solvent while tetrahydrofuran gave inferior results.Similar solvent effects were observed in the additions of various Grignard reagents to 1a, which afforded γ-lactones 2, 3, 12, and 13 in moderate trans-selectivity.The best solvent for these reactions was dichloromethane.The 1,3-induction of cuprate additions was studied by using aldehydes 8a-8c.The results obtained were interpreted in terms of chelate-controlled additions with formation of seven-membered ring chelates which involve both carbonyl functions of aldehyde 1 or 8.The function of ester groups as effective ligands of lithium or MgX cations may also be of importance for other stereoselective reactions employing organometallic reagents.

A Chelate-Controlled Route to Disubstituted and Tetrasubstituted γ-Lactones Stereoselectivity in Lewis Acid Promoted Additions to Chiral Methyl β-Formylcarboxylates

On reaction with allyltrimethylsilane/TiCl4, chiral methyl β-formylcarboxylates 1a - 1h provide disubstituted and tertasubstituted γ-lactones 3a - 3h with moderate to excellent diastereoselectivities.Other Lewis acids are less selective.The formation of seven-membered ring chelates 1.TiCl4 has been proven unambiguously by NMR spectroscopy in several cases.Trichloromethyltitanium displays a selectivity pattern similar to the reagent combination allylsilane/TiCl4.Aldehydes 1a - 1d, 1g, and 1h give primarily trans-γ-lactones, whereas under appropriate conditions 1f affords an excess of cis-γ-lactone 3f.These results are discussed with regard to the Felkin-Anh model and to chelate formation.Model studies with simpler chiral aldehydes 5 and 7 as well as with acetals 9a/b and 11a/b are presented and discussed.They emphasize the importance of chelate control in additions to β-formyl esters 1. - Key Words: γ-Lactones, di- and tetrasubstituted / Chelates, seven-membered / Allylsilane additions, Lewis acid promoted / Felkin-Anh model / Aldehydes, chiral