Organocatalytic Dimerization of Succinaldehyde

Author:

Bennett Steven H.,Aggarwal* Varinder K.

Abstract

AbstractThis chapter describes the organocatalytic dimerization of succinaldehyde. Mechanistically, the dimerization process proceeds through the formation of an anti‐enamine with succinaldehyde and L‐proline, followed by pseudo‐equatorial approach of a second succinaldehyde to give trialdehyde 5 via transition state 4. The chapter presents some of the important points to be considered, the conditions that need to be maintained, characterization data, and the reagents required, as well as the techniques used and the equipment setup that are vital to carrying out the process. It also describes the hazards associated with working with chemicals and the ways to deal with these hazards.

Publisher

Wiley

Reference29 articles.

1. School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS United Kingdom; orcid.org/0000‐0003‐0344‐6430; Email:v.aggarwal@bristol.ac.uk. The authors thank EPSRC (EP/M012530/1) for financial support and Dr. Andrejs Pelšs (Latvian Institute of Organic Synthesis) for helpful discussions.

2. Prostaglandin Total Synthesis Enabled by the Organocatalytic Dimerization of Succinaldehyde

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4. Morpholinium Trifluoroacetate-Catalyzed Aldol Condensation of Acetone with both Aromatic and Aliphatic Aldehydes

5. Reoptimization of the Organocatalyzed Double Aldol Domino Process to a Key Enal Intermediate and Its Application to the Total Synthesis of Δ12 -Prostaglandin J3

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