138751-07-2

Upstream product

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

Downstream Products

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

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

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.