Related Experiment Video
Updated: Jun 4, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Asymmetric synthesis of ethoxydienamines in superbasic medium mediated by chiral sulfinyl group
Marco Blangetti1, Gianluca Croce, Annamaria Deagostino
1Dipartimento di Chimica Generale e Chimica Organica, Università degli Studi di Torino, Via P. Giuria, 7-10125 Torino, Italy.
Abstract:
The direct addition of metalated alkoxydiene 2, obtained from α,β-unsaturated acetal 1 through a LIC-KOR-promoted conjugated elimination reaction, to enantiopure sulfinimines 3 (both R and SN-sulfinyl imines) afforded N-sulfinyl alkoxydienyl amines 4 with high diastereoselectivity. Functionalized enantiopure alkoxydienyl amines 5 were then easily obtained upon the selective removal of the chiral auxiliary under mild conditions. Moreover, the further hydrolysis of the alkoxydienyl moiety gave access to protected enantiopure β-keto amines 7.
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Sharpless Epoxidation
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
