Pd-Catalyzed kinetic resolution of cyclic enol ethers. An enantioselective route to functionalised pyrans
Jean-Olivier Zirimwabagabo1, Joseph P A Harrity
1Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK. j.harrity@sheffield.ac.uk.
Abstract:
Functionalised cyclic enol ethers can be recovered with high levels of enantiocontrol after an asymmetric catalytic [1,3]-rearrangement reaction. These compounds can be further elaborated to a series of carbo- and heterocyclic products in good yield and with excellent levels of stereocontrol.
Related Concept Videos
Thermal and Photochemical Electrocyclic Reactions: Overview
Regioselective Formation of Enolates
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Reactivity of Enols

![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)
