138751-07-2

Upstream product

• 133030-44-1 (2RS,3SR)-2,6-dimethylphenyl 3-hydroxy-2-methyl-3-<1-(phenylthio)cyclopentyl>propionate 
• 115205-40-8 1-phenylsulfanylcyclopentane carboxaldehyde 
• 138649-96-4 (4S)-3-<(2S,3S)-3-hydroxy-2-methyl-1-oxo-3-(1-phenylsulfanylcyclopentyl)propyl>-4-phenylmethyl-1,3-oxazolidin-2-one 

Downstream Products

• 120749-38-4 (3RS,4SR)-3-methyl-4-phenylthio-1-oxaspiro<4.4>nonane 
• 133030-63-4 (1RS,2RS)-3-(t-butyldiphenylsiloxy)-2-methyl-1-<1-(phenylthio)cyclopentyl>propan-1-ol 
• 133030-73-6 (1RS,2'SR)-(E)-2-<3'-(t-butyldiphenylsiloxy)-2'-methylpropylidene>cyclopentanol 
• 133030-68-9 (1'RS,2'SR)-1-<3'-(t-butyldiphenylsiloxy)-2'-methyl-1'-(phenylthio)propyl>cyclopentene 
• 133030-72-5 (1RS,2RS)-3-(t-butyldiphenylsiloxy)-1-(cyclopent-1-enyl)-2-methylpropyl phenyl sulphoxide 
• 138751-05-0 (3R,4R)-3-methyl-4-phenylsulfanyl-1-oxa-spiro<4.4>nonane 

Relevant academic research and scientific papers

The stereoselective synthesis of oxetanes; exploration of a new, Mitsunobu-style procedure for the cyclisation of 1,3-diols

A solution of 2-methyl-3-[1-(phenylsulfanyl)cyclohexyl]propane-1,3-diol 1 in toluene treated with triphenyl-phosphine, Ziram 2 and DEAD, gave 3-methyl-2-[1-(phenylsulfanyl)cyclohexyl]oxetane 3 in 85% yield. A mechanistic study has been undertaken, optimal conditions have been found and the range of substrates for which the reaction is useful has been explored. We include the results of an X-ray study which shows that compound 33 (the oxidation product of diol 1) is a sulfone rather than a sulfoxide as previously reported.

Asymmetric aldol reactions of achiral 2-phenylsulfanyl aldehydes with small- and medium-sized carbocyclic rings: the synthesis of homochiral spirocyclic lactones, pyrrolidines and tetrahydrofurans

Chiral boron enolates based on the 1,3-oxazolidin-2-one auxiliary react with achiral 1-phenylsulfanylcycloalkanecarbaldehydes in anti- and syn-selective aldol processes to give the corresponding aldol products with moderate to excellent levels of diastereo- and enantio-control.Stereospecific cyclisation via an asymmetric episulfonium (thiiranium) ion leads to optically pure spirocyclic compounds in high chemical yields.

Asymmetric synthesis of spirocyclic pyrrolidines and tetrahydrofurans by chiral aldol reactions and phenylthio migration

Highly enantioselective aldol reactions of the boron enolate of (S)-N-propionyl-4-(phenylmethyl)-2-oxazolidinone with α-phenylthio cycloalkanecarbaldehydes were achieved. Cyclisation of the chiral phenylthiosulphonamide and diols gave the title compounds in excellent yields and enantiomeric excess.

Transformation of Cyclic α-Phenylthio Aldehydes by Stereoselective Aldol Reactions and Phenylthio Migration into Spirocyclic Lactones and Ethers, and E-Allylic Alcohols with 1,4-Related Chiral Centres

syn- and anti-Selective aldol reactions between enolates of propionate esters and three α-phenylthio cycloalkanecarbaldehydes give single diastereoisomers of phenylthio alcohols which rearrange in acid with 5-hydroxy or 5-CO2H participation to give spiroc