Related Experiment Video
Updated: Jul 17, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Enantioselective Michael Addition of Malononitrile to Unsaturated Ketones Catalyzed by Rare-Earth Metal Amides
Yingying Ren1, Qishun Yu1, Chengrong Lu1
1College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Organic Synthesis of Jiangsu Province, Soochow University, Suzhou 215123, People's Republic of China.
Abstract:
The catalytic enantioselective Michael addition of α,β-unsaturated ketones with malononitrile was well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = Y, Eu, Sm, Nd, La) with chiral phenoxy-functionalized TsDPEN ligands. The combination of lanthanum amide La[N(SiMe3)2]3 and chiral TsDPEN ligand H3L1 [H3L1 = N-((1R,2R)-2-((3,5-di-tert-butyl-2-hydroxybenzyl)amino)-1,2-diphenylethyl)-4-methylbenzenesulfonamide] in a 1:1.5 molar ratio was proved to be the optimal partner in THF, which provided the desired β-carbonyl dinitriles in excellent yields and good to high enantioselectivities after 12 h at -15 °C.
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
α-Alkylation of Ketones via Enolate Ions
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Nucleophilic Aromatic Substitution: Elimination–Addition
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

