Related Experiment Video
Updated: Jul 11, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis and analysis of thio-, thiono-, and dithio-derivatives of whiskey lactone
H G Schmarr1, W Eisenreich, K H Engel
1Lehrstuhl für Allgemeine Lebensmitteltechnologie, Technische Universität München, Am Forum 2, D-85350 Freising-Weihenstephan, Germany. hg.schmarr@wzw.tum.de
Abstract:
Cis- and trans-3-methyl-4-octanolide (1, whiskey lactones) were converted into their thio- (2), thiono- (3), and dithio- (4) derivatives by reaction with phosphorus pentasulfide. The reaction products were characterized by GC-mass spectrometry, (1)H NMR spectroscopy, and GC-olfactometry. Two-dimensional NOESY spectra showed that sulfur is incorporated into the ring with reversal of the absolute configuration at C-4, whereas substitution of the keto-oxygen atom by sulfur occurs with retention of ring configuration. The cis- and trans-pairs of 2, 3, and 4 were separated into enantiomers by GC on heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin and heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin as chiral stationary phases. GC-olfactometry revealed a sweet coconut-like odor for the cis-thio- and pleasant mushroom-like flavors for the cis-thiono- and trans-dithio-derivatives of whiskey lactone.
Related Concept Videos
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Preparation and Reactions of Thiols
Preparation and Reactions of Sulfides
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Alkylation of β-Diester Enolates: Malonic Ester Synthesis

