Related Experiment Video
Updated: May 24, 2025
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Asymmetric Synthesis of Functionalized 2-Isoxazolines
Beyza Hamur1, Fatma Albayrak Halac1, Fethiye Yilmazer1
1Department of Chemistry, College of Science, Gebze Technical University, 41400 Gebze, Kocaeli, Turkey.
Abstract:
The asymmetric synthesis of the isoxazoline skeleton was achieved by the oxidation of hydroxylaminoalkyl furan prepared from simple starting materials: 2-methylfuran and (S)-epichlorohydrin. The synthesis features an NBS-mediated oxidation of hydroxylaminoalkyl furan to give an α,β-unsaturated ketone intermediate which cyclized to the isoxazoline. The α,β-unsaturated double bond was successfully cleaved with RuCl3·xH2O catalysis en route to the isoxazoline skeleton bearing alcohol, aldehyde, and carboxylic acid functionalities.
More Related Videos
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
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...