898541-20-3

Upstream product

• 89-82-7 pulegone 
• 100-53-8 phenylmethanethiol 

Downstream Products

• 79563-59-0 (-)-(1R,2R,5R)-5-methyl-2-(1-mercapto-1-methylethyl)-cyclohexan-1-ol 
• 622840-40-8 8-mercaptomenthol 
• 79563-67-0 (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol 
• 79563-68-1 (1R,2S,5R)-2-(1-Mercapto-1-methyl-ethyl)-5-methyl-cyclohexanol 

Relevant academic research and scientific papers

Perchloric acid impregnated on silica gel (HClO4/SiO 2): A versatile catalyst for Michael addition of thiols to the electron-deficient alkenes

Perchloric acid adsorbed on silica gel (HClO4X/SiO2) has been found to be a highly efficient and versatile catalyst for the Michael addition of thiols to a wide variety of conjugated alkenes such as α,α-unsaturated ketones, carboxylic esters, nitriles, amides and chalcones in dichloromethane or methanol at room temperature. The reactions are completed within 2-20 min in high yields. Some of the additional advantages are: no aqueous work-up is necessary, and the catalyst is also reusable. Moreover, the solid product can be obtained without chromatographic separation. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

New reagent for the optical resolution of ketones: (-) (1R, 2R, 5R)-5-methyl-2-(1-mercapto-1-methylethyl)-cyclohexanol. Application to trans dimethyl cyclopentanone-3,4-dicarboxylate

(-) (1R, 2R, 5R)-5-methyl-2-(1-mercapto-1-methylethyl)-cyclohexanol was shown to be a very powerful agent for the optical resolution of ketones. It was used for the resolution of trans dimethyl cyclopentanone-3,4-dicarboxylate combined with the epimerizat

Asymmetric Syntheses Based on 1,3-Oxathianes. 2. Synthesis of Chiral Tertiary α-Hydroxy Aldehydes, α-Hydroxy Acids, Glycols (RR'C(OH)CH2OH), and Carbinols (RR'C(OH)CH3) in High Enantiomeric Purity

A chiral 1,3-oxathiane (5) prepared from (+)-pulegone in three steps is converted to diastereomerically pure equatorial 2-acyl derivatives by lithiation, condensation with aldehydes, and Me2SO oxidation.Reaction of the resulting ketones with Grignard reagents at -78 deg C again proceeds highly stereoselectively (diastereomer excess generally above 90percent) according to Cram's rule (cyclic model).The resulting tertiary carbinols when cleaved with NCS/AgNO3 give chiral tertiary α-hydroxy aldehydes, RR'C(OH)CHO, plus a mixture of epimeric sultines which may be readily reconverted to the starting oxathiane.The hydroxy aldehydes have been oxidized to chiral tertiary α-hydroxy acids, RR'C(OH)CO2H, and reduced to primary-tertiary glycols, RR'C(OH)CH2OH, and further to tertiary carbinols, RR'C(OH)CH3, all with over 90percent ee.The opposite enantiomers of these compounds (again >90percent ee) may be obtained by starting with a diastereomeric 1,3-oxathiane (6), also available from (+)-pulegone.The configurations of the chiral products may be deduced from the manner of preparation and the assumption that Cram's rule is valid and agree with prior assignments in the literature.

ASYMMETRIC SYNTHESIS OF (R)-(+)-ETHYLMETHYL-n-PROPYLCARBINOL IN HIGH ENANTIOMERIC PURITY. A 1,3-OXATHIANE DERIVED FROM (+)-PULEGONE AS CHIRAL ADJUVANT

A chiral, conformationally locked 1,3-oxathiane has been prepared by 1,4-addition of benzyl mercaptan to (+)-pulegone followed by Na/NH3 reduction and condensation of the resulting hydroxythiol with paraformaldehyde.The utility of this chiral adjuvant is