22865-14-1

Upstream product

• 22524-25-0 1-phenylhex-5-en-1-one 
• 1120-72-5 2-Methylcyclopentanone 
• 100-58-3 phenylmagnesium bromide 
• 22865-01-6 (R,R)-1-phenyl-2-methylcyclopentanol 
• 112927-82-9 5-Iodo-2-methyl-1-phenyl-pentan-1-one 
• 93-89-0 benzoic acid ethyl ester 
• 63452-95-9 1,4-bis(bromomagnesio)pentane 

Downstream Products

• 4810-10-0 1-(2-methylcyclopent-1-enyl)benzene 
• 4810-11-1 1-phenyl-5-methylcyclopentene 
• 22865-01-6 (R,R)-1-phenyl-2-methylcyclopentanol 

Relevant academic research and scientific papers

Reductive cyclization of enones by titanium(IV) aryloxide and a Grignard reagent

The titanium-mediated cyclization of δ,ε-enones by using dichlorotitanium diphenoxide-cyclohexylmagnesium chloride diastereoselectively afforded cis-substituted cyclopentanols and was thus found to parallel the stoichiometric and catalytic titanocene-mediated reactions.

Mechanisms of solvolytic elimination reactions of tertiary substrates: Stereospecific 1,2-elimination reactions

Solvolysis of (R,S)-1-chloro-1-(fluoren-9-yl)-2-methylcyclopentane (1-Cl) or the analogous 3,5-dinitrobenzoate ester 1-DNB in largely aqueous solutions yields alkenes 1-(fluoren-9-yl)-2-methylcyclopentene (4) and 1-(fluoren-9-yl)-5-methylcyclopentene (5)

Stereoselective nickel and manganese catalyzed cyclizations of 5-haloketones

The treatment of various 5-iodoketones or 5-bromoketones with Et2Zn in the presence of either Ni(acac)2 (5 mol %) or MnBr2/ CuCl (5 mol %) produces functionalized substituted cyclopentanols bearing in some cases contiguous

ω-Alkenyl-α-methoxy-benzyllithiums : Original synthesis and reactivity

1-Methoxy-benzyllithiums bearing suitably positioned C,C double bonds possess a high propensity to produce a five or a six membered cycle by carbocyclisation reaction. The reaction proceeds completely stereoselectively and produces a five membered cycle possessing the cis-stereochemistry between the methoxy and the adjacent methyl group.

Stereochemical Investigations of Samarium(II) Iodide-Promoted 5-Exo and 6-Exo Ketyl-Olefin Radical Cyclization Reactions

Samarium(II) iodide (SmI2)-promoted ketyl cyclizations of several substituted, unsaturated ketones, providing various cyclpentyl and cyclohexyl systems, have been investigated.The resulting experiments provide stereochemical insight into these reactions and in addition outline the synthetic potential of these 5-exo and 6-exo radical cyclization processes.

RELATIVE ASYMMETRIC INDUCTION IN FORMATION OF SUBSTITUTED CYCLOPENTANOLS VIA INTRAMOLECULAR CARBONYL ADDITIONS

Relative asymmetric induction in intramolecular carbonyl addition reactions has been studied for the first time in a systematic fashion.An empirical model has been proposed to rationalize the results.

A Highly Stereoselective Synthesis of Trans-1,2-Disubstituted Cycloalkanols

The study of the reactions of 1,4-bis(bromomagnesio)pentane, 1,1-bis(bromomagnesio)hexane, 1,4-bis(bromomagnesio)heptane, and 1,4-bis(bromomagnesio)octane with aliphatic and aromatic carboxylic acid esters in tetrahydrofuran solution was undertaken in order to ascertain which factors influence isomer distribution.The yields of this annelation processes are in the range of 68-88percent.The formation of trans OH 1,2-disubstituted cyclopentanols having the alkyl groups cis is generally observed with yields of 77-96percent.The reaction of 1,5-bis(bromomagnesio)hexane with carboxylicacid esters is less stereoselective and is more influenced by steric effects.

Reaction of 1,4-Bis(bromomagnesio)pentane and 1,5-Bis(bromomagnesio)hexane with Carboxylic acid Esters. A Useful, Highly Stereoselective Annelation

1,4-Bis(bromomagnesio)pentane and 1,5-bis(bromomagnesio)hexane have been prepared in THF solution, when treated with carboxylic acid esters, they afford trans diastereomeric bisubstituted cycloalkanols via a highly diastereoselective intramolecular Grignard reaction.