The Reaction of Selenium Dioxide with Levulinates

Raymond, Samuel

doi:10.1021/ja01163a526

Cited by 7 publications

(1 citation statement)

References 2 publications

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“…The appearance of α,β-unsaturated-γ-keto ester functionalities in a variety of natural products coupled with the rich reactivity of this functional group have stimulated interest in the preparation of this functionality. Methods reported for the preparation of α,β-unsaturated-γ-keto esters include the conversion of γ-keto esters to the α,β-unsaturated systems via selenium dioxide oxidation, bromination of γ-keto esters, followed by elimination with base, Horner−Emmons chemistry between α-formyl esters and β-keto phosphonates, oxidation of furan skeletons, and laborious multistep syntheses …”

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confidence: 99%

Zinc Carbenoid-Mediated Chain Extension: Preparation of α,β-Unsaturated-γ-keto Esters and Amides

Ronsheim

Zercher

2003

J. Org. Chem.

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An efficient one-pot preparation of alpha,beta-unsaturated-gamma-keto esters and amides has been developed. A zinc carbenoid-mediated chain extension of a beta-dicarbonyl substrate provides access to an intermediate zinc enolate, which is treated sequentially with a halogen and amine base. This method has been applied to a variety of ester and amide starting materials, as well as to amino acid-derived substrates and to a formal synthesis of (R,R)-(-)-pyrenophorin.

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confidence: 99%

Zinc Carbenoid-Mediated Chain Extension: Preparation of α,β-Unsaturated-γ-keto Esters and Amides

Ronsheim

Zercher

2003

J. Org. Chem.

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Selenium Dioxide Oxidation

Rabjohn

2011

Organic Reactions

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Selenium dioxide has developed considerable stature since it was first reviewed in this series. Search for examples of oxidation by selenium dioxide or selenious acid is difficult because the terms are seldom indexed. Frequently it is difficult to decide whether selenium dioxide or selenious acid was the oxidizing agent employed in a reaction because it is impossible to determine if water was present. The determination is complex because the free acid or anhydride may react reversibly or irreversibly with various solvents such as alcohols or acids. To give selenium‐containing compounds of unknown structure which might be the real oxidizing gents. In this chapter, the practical aspects of oxidation with selenium dioxide are summarized. Mechanisms are treated in detail.

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