Title

A Highly Enantioselective [4+2] Cycloaddition Involving Aldehydes and Β,ƴ-unsaturated-α-keto Esters

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Summer 2016

Abstract

A stereoselective inverse electron demand oxo-Diels-Alder reaction between electron poor diene (γ-aryl-β,γ-unsaturated-α-keto ester) and electron rich dienophile has been studied. This type of cycloaddition reaction is extremely useful for the construction of O-, N-, S-centered heterocyclic compounds, which are routinely used in both organic and medicinal chemistry. The [4+2] hetero cycloaddition involving various aldehydes and β,Ƴ-Unsaturated-α-keto esters was carried out in which three different types of proline substituted catalysts were used. For these reactions, high selectivities, (enantiomeric excess 80% - 98%) were obtained using Catalyst 3. Owing to the bulkiness of Catalyst 3, compared to the other catalysts tested, it is more efficient at catalyzing these type reactions.

Advisor

Allan D Headley

Subject Categories

Chemistry | Physical Sciences and Mathematics

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