Related Experiment Video
Updated: Jul 3, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Synthesis and application of easily recyclable thiomorpholines for use in sulfur ylide mediated asymmetric
Markus Hansch1, Ona Illa, Eoghan M McGarrigle
1School of Chemistry, University of Bristol, Cantock's Close, UK.
Abstract:
Chiral nonracemic thiomorpholines have been synthesized in four to six steps from limonene or achiral alkenes using alpha-methylbenzylamine to control absolute stereochemistry. These aminosulfides have been used to generate sulfur ylides, which have been applied in the asymmetric epoxidation of aldehydes as easily recoverable catalysts. Excellent yields (up to 98 %), enantioselectivities (up to 97:3 e.r.), and diastereoselectivities (>or=98:2 trans/cis) were achieved in these epoxidations and the sulfides were easily recovered in high yield (up to 97 %) by simple acid/base extraction.
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Sharpless Epoxidation
Conversion of Alcohols to Alkyl Halides
