95864-69-0

Upstream product

• 84884-00-4 2-Hydroxy-1-methylcyclopentancarbonsaeure-methylester 
• 58101-60-3 methyl cyclopent-3-ene-1-carboxylate 
• 74-88-4 methyl iodide 

Downstream Products

• 115678-58-5 methyl 1-(phenylsulfonyl)-4-methylcyclopentene-4-carboxylate 
• 114430-20-5 (2aS,3aS,5R,6aS,7aS)-6a-Benzenesulfonyl-2a,5-dimethyl-7-oxo-decahydro-cyclobuta[f]indene-5-carboxylic acid methyl ester 
• 114430-20-5 (2aR,3aS,5R,6aS,7aR)-6a-Benzenesulfonyl-2a,5-dimethyl-7-oxo-decahydro-cyclobuta[f]indene-5-carboxylic acid methyl ester 
• 115678-36-9 (2R,3aR,7aR)-3a-Benzenesulfonyl-2,6-dimethyl-4-oxo-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylic acid methyl ester 
• 115678-36-9 methyl (2S^*,3aS^*,7aS^*)-3a,4,7,7a-tetrahydro-2,6-dimethyl-4-oxo-3a-(phenylsulfonyl)-2-indancarboxylate 
• 115678-39-2 (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-2a,5-dimethyl-7-trifluoromethanesulfonyloxy-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester 
• 115678-42-7 (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Copper-catalyzed desymmetrization of prochiral 4,4-disubstituted cyclopentenes: Via a site-selective allylic oxidation: A concise total synthesis of untenone A

The desymmetrization of prochiral 4,4-disubstituted cyclopentenes via a site-selective copper-catalyzed allylic oxidation is described. This study provides a direct comparison of a series of known methods for allylic oxidation, and thus identifies ligand-free copper(i) iodide as the optimal catalyst for this particular process. Notably, this work offers a convenient approach to the preparation of γ-quaternary α,β-unsaturated cyclopentenones, which permits an efficient three-step total synthesis of (±)-untenone A.

Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons

Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.

Synthesis and Rearrangement of Substituted Bicyclopent-2-enes. A Thermal "Walk"-Rearrangement

The synthesis and the thermal behaviour of methyl 5-methyl-, 1,5-, and 2,5-dimethylbicyclopent-2-ene-5-carboxylates 3a,b, 4a,b, 5a,b, as well as of 1,5- and 2,5-dimethylbicyclopent-2-ene-5-carbonitriles 6a, 7a,b are reported.The "walk"-rearrangement which is degenerate in the cases of 3a,b could be detected experimentally with the aid of the dimethyl derivatives 4a,b, 5a,b, 6a, and 7a,b.Electrocyclic ring opening to the correspondingly substituted 1,3-cyclopentadienes competes with the "walk"-rearrangements.Already at 0 deg C the "walk"-rearrangements 4a -> 5a, 4b -> 5b, and 6a -> 7a proceed stereospecifically with inversion at the migrating carbon atom C-5 as postulated by Woodward and Hoffmann (0 deg C: ΔG*= 21.7, 24.8, and 21.9 kcal/mol).We assume that the surprisingly low activation barriers do not only result from the resonance stabilization of an aromatic transition state but largely from the anomalously high ground-state enthalpy of the bicyclopentene system.