40564-46-3

Upstream product

• 300-57-2 allylbenzene 
• 292638-85-8 acrylic acid methyl ester 
• 111183-88-1 5-oxo-6-phenylhexanal 
• 15507-35-4 1-benzylcyclopentene 
• 2015-57-8 1-benzylcyclopentanol 
• 61077-65-4 1-phenylpent-4-en-2-ol 
• 122-78-1 phenylacetaldehyde 
• 120-92-3 cyclopentanone 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 69815-09-4 (+/-)-1-Benzyl-5-methyl-1,5-hexandiol 

Relevant academic research and scientific papers

One-pot sequential 1,4- and 1,2-reductions of α,β-unsaturated δ-lactones to the corresponding δ-lactols with CuCl and NaBH 4 in methanol

An efficient, one-pot method for the highly chemoselective synthesis of δ-lactols from α,β-unsaturated δ-lactones using CuCl and NaBH4 in methanol was developed. Georg Thieme Verlag Stuttgart. New York.

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.

Cooperative Catalysis of Samarium Diiodide and Mercaptan in a Stereoselective One-pot Transformation of 5-oxopentanals into δ-lactones

(Matrix Presented) We demonstrate a general method for conversion of various 5-oxopentanals to substituted δ-lactones and 1-oxa-2-decalones by the synergistic catalysis of samarium diiodide and 2-propanethiol (or disulfide). The deliberate use of mercaptan is advantageous to facilitate the catalytic cycle. This method shows high stereoselectivities, and an enantioselective procedure is feasible by using the chiral mercaptan (1R,2S)-1-phenyl-2-(N-acetamido)propanethiol as a promoter.

PHASE TRANSFER CATALYSIS AND HOMOGENEOUS REACTIONS WITH β-OXYALKYL RADICALS FROM ORGANOMERCURIALS

β-Alkoxy- and β-hydroxyalkyl radicals generated by sodium borohydride reduction of oxymercurials react with electron deficient olefins to give addition compounds in a homogeneous process.Heterogeneous reactions are also successful in the presence of catalytic amounts of surfactants and provide a superior method for the "one pot" reductive alkylation of oxymercurials.