ScholarLens Back to search
2010•Angewandte Chemie International EditionRequires access

The Elusive Enamine Intermediate in Proline‐Catalyzed Aldol Reactions: NMR Detection, Formation Pathway, and Stabilization Trends

Markus B. Schmid, Kirsten Zeitler, Ruth M. Gschwind

Open publisher page 173 citations

Abstract

The missing link: The elusive enamine intermediate of nucleophilic proline catalysis was detected and stereochemically characterized by NMR analysis of the aldehyde self-aldolization reaction in dipolar aprotic solvents. NMR exchange spectroscopy (EXSY) was used to observe direct enamine formation from oxazolidinones. Additionally, the stabilization of the intermediate by the appropriate choice of solvent and substitution pattern on the aldehyde is presented.

About this research paper

What this paper is about

The missing link: The elusive enamine intermediate of nucleophilic proline catalysis was detected and stereochemically characterized by NMR analysis of the aldehyde self-aldolization reaction in dipolar aprotic solvents. NMR exchange spectroscopy (EXSY) was used to observe direct enamine formation from oxazolidinones. Additionally, the stabilization of the intermediate by the appropriate choice of solvent and substitution pattern on the aldehyde is presented.

Why it matters

OpenAlex reports 173 citations for this work. Citation counts describe recorded attention and do not establish research quality.

Key contribution

A contribution statement is not available in the OpenAlex record.

Method / approach

Method details are not available in the OpenAlex metadata.

Main findings

Findings are not separately available in the OpenAlex metadata.

Limitations

Limitations are not available in the OpenAlex metadata.

Applications

Application details are not available in the OpenAlex metadata.

Available abstract

The missing link: The elusive enamine intermediate of nucleophilic proline catalysis was detected and stereochemically characterized by NMR analysis of the aldehyde self-aldolization reaction in dipolar aprotic solvents. NMR exchange spectroscopy (EXSY) was used to observe direct enamine formation from oxazolidinones. Additionally, the stabilization of the intermediate by the appropriate choice of solvent and substitution pattern on the aldehyde is presented.

Key concepts: Enamine, Aldol reaction, Chemistry, Aldehyde, Catalysis, Organocatalysis, Nucleophile, Proline

Related papers

Related paper 1Related paper 2Related paper 3
Back to paper searchBrowse research topicsOriginal source
The Elusive Enamine Intermediate in Proline‐Catalyzed Aldol Reactions: NMR Detection, Formation Pathway, and Stabilization Trends — Research Paper | ScholarLens