138751-06-1

Upstream product

• 104750-41-6 (1RS,2RS)-2-methyl-1-<1-(phenylthio)cyclohexyl>propane-1,3-diol 
• 104750-41-6 (1R,2S)-2-Methyl-1-(1-phenylsulfanyl-cyclohexyl)-propane-1,3-diol 
• 53282-55-6 (trimethylsiloxymethylidene)cyclohexane 
• 57768-35-1 1-(phenylthio)-1-cyclohexanecarboxaldehyde 
• 2043-61-0 cyclohexanecarbaldehyde 
• 138751-08-3 (1S,2S)-2-methyl-1-(1-phenylsulfanylcyclohexyl)propane-1,3-diol 
• 138649-97-5 (4S)-3-<(2S,3S)-3-hydroxy-2-methyl-1-oxo-3-(1-phenylsulfanylcyclohexyl)propyl>-4-phenylmethyl-1,3-oxazolidin-2-one 
• 104750-47-2 (2R,3R)-3-Hydroxy-2-methyl-3-(1-phenylsulfanyl-cyclohexyl)-propionic acid methyl ester 
• 104750-38-1 (2RS,3SR)-2,6-dimethylphenyl 3-hydroxy-2-methyl-3-<1-(phenylthio)cyclohexyl>propionate 

Relevant academic research and scientific papers

Kinetic and thermodynamic control in the stereospecific synthesis of cyclic ethers via phenylsulfanyl (PhS) migration

The factors controlling the stereospecific cyclisation of 1,3-diols with PhS migration to give THFs rather than oxetanes are reassessed in the light of evidence that these reactions are under thermodynamic control. Rearrangement of cyclic sulfites gives the nearest approach to kinetic control.

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.

Rearrangements of phenylthio substituted 1,n-diols with toluene-p-sulfonic acid and with toluene-p-sulfonyl chloride

Rearrangement of a series of 1,n diols (n = 2 to 12), one OH group having an adjacent PhS group, under the two sets of conditions in the title, gives single compounds in high yields drawn drom four possible classes of product. The effects of chain length

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

STEREOCHEMICAL CONTROL IN THE SYNTHESIS OF TETRAHYDROFURANS BY CYCLISATION OF DIOLS WITH PHENYLTHIO MIGRATION

Cyclisation of diols with PhS migration leads to tetrahydrofurans by inversion at both the migration origin and terminus.Cyclisation to a secondary migration terminus is controlled by stereochemical factors.

PHENYLTHIO(PhS) MIGRATION IN THE STEREOCONTROLLED SYNTHESIS OF ALLYLIC ALCOHOLS WITH 1,4 RELATED CHIRAL CENTRES.

Stereoselective aldol products are transformed by PhS migration into lactones, tetrahydrofurans, and, by subsequent Evans-Mislow rearrangement, into the title compounds with complete stereochemical control.