82909-44-2

Upstream product

• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 108-98-5 thiophenol 
• 56671-87-5 3-Bromo-2-methylcyclopent-2-en-1-one 
• 5870-63-3 3-hydroxy-2-methyl-2-cyclopenten-1-one 
• 917-54-4 methyllithium 
• 67-56-1 methanol 

Downstream Products

• 123487-89-8 2-Methyl-3-(phenylsulfonyl)cyclopent-2-en-1-one 
• 96530-16-4 2-methyl-3-phenylthio-2-cyclopentenol 
• 102061-46-1 2,4-dimethyl-1-phenylthiocyclopentene 
• 102061-47-2 3,5-dimethyl-2-phenylthio-2-cyclopentenone 
• 102061-44-9 2,5-dimethyl-3-phenylthio-2-cyclopentenol 
• 123488-07-3 1-(Phenylsulfonyl)-3-methylene-5-methyl-6-(methoxymethoxy)-cis-bicyclo<3.3.0>octane 
• 123488-07-3 1-(Phenylsulfonyl)-3-methylene-5-methyl-6-(methoxymethoxy)-cis-bicyclo<3.3.0>octane 
• 123487-83-2 (3-Benzenesulfonyl-2-methyl-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane 
• 123487-84-3 (3-Methoxymethoxy-2-methyl-cyclopent-1-enesulfonyl)-benzene 
• 123487-90-1 2-Methyl-3-(phenylsulfonyl)cyclopent-2-en-1-ol 
• 96530-12-0 3-methyl-2-phenylthio-2-cyclopentenone 
• 96530-14-2 2-methyl-1-phenylsulfonylcyclopentene 
• 96530-15-3 2-methyl-1-phenylsulfinylcyclopentene 
• 67957-90-8 1-(phenylthio)-2-methylcyclopentene 

Relevant academic research and scientific papers

Asymmetric allylic alkylation of cyclic vinylogous esters and thioesters by Pd-catalyzed decarboxylation of enol carbonate and β-ketoester substrates

(Chemical Equation Presented) Excellent yields and enantioselectivities were achieved for the palladium-catalyzed asymmetric allylic alkylation of vinylogous thioesters. The close-to-neutral reaction conditions ensure that this reaction can tolerate a wide range of functionalities. Furthermore, this approach provides a convenient protocol for the synthesis of synthetically important α,α- and γ,γ-di-substituted cycloalkenones.

Moenomycin A: New chemistry that allows to attach the antibiotic to reporter groups, solid supports, and proteins

Moenomycin A (18) on reaction with the diazonium salt derived from bifunctional (protected) 15 yields the coupling product 19 which on reduction is converted into the moenomycin thiol derivative 21. Thiol 21 has been used to prepare selectively moenomycin dansyl and biotin adducts 26 and 28, respectively. This work was performed with the aim to use moenomycin as a tool for studies of the transglycosylation step in peptidoglycan biosynthesis.

A Stereocontrolled Cyclopentenone Synthesis via Cycloaddition

γ-Alkoxy-α,β-unsaturated sulfones are readily available in both racemic and scalemic form, the latter either by asymmetric induction from achiral building block or from readily available scalemic starting materials.These electron deficient olefins serve as excellent substrates for cycloaddition involving the intermediacy of trimethylenemethane-palladium complexes.The highly diastereoselective methylenecyclopentannulation provides a versatile cycloadduct that allows very simple conversion to cyclopentenones and cyclopentadienes and the synthetic equivalent ofaddition to cycloalkanones and alkynones, two classes of substrate that either frequently give low yields or totally fail in palladium-catalyzed cycloadditions from 2-(acetoxymethyl)-3-(trimethylsilyl)prop-1-ene.

Reduction of Vinylogous Thioesters with Lithium Aluminum Hydride. I. Reduction of β-Phenylthio-α,β-unsaturated Cyclic Ketones

5,5,Dimethyl-3-phenoxy-2-cyclohexenone (Ib) was reduced with lithium aluminum hydride (LAH) to give the 1,2-addition product (IIIa). 2-Methyl-3-phenoxy-2-cyclopentetnone (IIa) gave a mixture of the allyl alcohol (IVa) and 1,2-addition product (IVb).On the

Reaction of β-halo α,β-unsaturated ketons with cuprate reagents. Efficient syntheses of β,β-dialkyl ketones and β-alkyl α,β-unsaturated ketones. A synthesis of (Z)-jasmone

Treatment of the 3-halo-2-cyclohexen-1-ones 11-15 and 17 with an excess of lithium dimethylcuprate provided good to excellent yields of the corresponding 3,3-dimethylcyclohexanones 21-24.Similar reactions involving the β-bromo cyclopentenones 19 and 20 stopped at the monoaddition stage, producing the cyclopentenones 40 and 43.Reaction of the β-bromo cyclohexenones 12 and 15 with 1.1 equiv. of lithium dimethylcuprate did not effect clean conversion of these substrates into the corresponding 3-methyl-2-cyclohexen-1-ones.When a series of β-bromo enones 12, 14-19were allowed to react with the lithium (phenylthio)(alkyl)cuprates 44-47, the correspondig β-alkyl enones were, in general, produced cleanly and efficiently.However, reaction of 3-bromo-2-methyl-2-cyclopenten-1-one (19) with the cuprate reagent 44 gave mainly the β-phenylthio enone 49.This undesired result could be avoided by employing, in the place of 19, The β-iodo cyclopentenone 50, which reacted smoothly with 44 to give a high yield of 2,3-dimethyl-2-cyclopenten-1-one (40).Reaction of 3-bromo-2-cyclohexen-1-one (14) with 3 equiv. of the mixed vinylcuprate reagent 48 gave 3-(3-butenyl)-2-cyclohexen-1-one (32).Alkylation of 1,3-cyclopentanedione with (Z)-1-chloro-2-pentene afforded compound 51, which was converted into the β-bromo enone 52.Treatment of the latter substance with lithium dimethylcuprate provided (Z)-jasmone (53).