Catalytic Enantioselective Synthesis of Oxazolines with Vinylogous Isocyano Esters
Cristian Guzmán-Cedillo1, Alicia Monleón-Ventura1, Amparo Sanz-Marco1
1Departament de Química Orgànica, Facultat de Química, Universitat de València, C. Dr. Moliner 50, 46100 Burjassot, Spain.
Abstract:
Vinylogous isocyano esters were prepared for the first time. They react with aldehydes to give chiral oxazolines bearing a pendant conjugated ester under synergistic silver/organocatalysis. The reaction is carried out using a bifunctional squaramide in combination with silver oxide and performs well with a number of aryl, heteroaryl, and cycloalkyl aldehydes, providing the expected heterocycles in good yields with good diastereoselectivity and enantiomeric excesses ranging from 60% to 95% ee.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
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...
Regioselective Formation of Enolates
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
