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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Preparation and Reactions of Sulfides02:26

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Cascade Cyclizations of α,β-Unsaturated Thioesters: Additional Examples.

Nicholas A Ahlemeyer1, Matthew R Straub1, David M Leace1

  • 1Department of Chemistry, Washington University, Campus Box 1134, One Brookings Drive, St. Louis, Missouri 63130, United States.

The Journal of Organic Chemistry
|December 14, 2020
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Summary
This summary is machine-generated.

This study details cascade cyclizations of alpha, beta-unsaturated thioesters using two pathways: enantioselective catalysis by amidine-based catalysts (ABCs) and a racemic mechanism involving thiolate nucleophiles.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Cascade cyclizations offer efficient synthetic routes.
  • Thioesters are versatile synthetic intermediates.
  • Understanding reaction mechanisms is crucial for catalyst design.

Purpose of the Study:

  • To report additional examples of cascade cyclizations of alpha, beta-unsaturated thioesters.
  • To elucidate the distinct mechanistic pathways involved.
  • To highlight the role of amidine-based catalysts (ABCs) and thiolate nucleophiles.

Main Methods:

  • Exploration of cascade cyclization reactions.
  • Mechanistic studies to differentiate reaction pathways.
  • Use of amidine-based catalysts (ABCs).
  • Investigation of thiolate-mediated reactions.

Main Results:

  • Successful demonstration of several new cascade cyclizations.
  • Identification of two distinct mechanistic pathways.
  • Enantioselective acyl transfer pathway promoted by ABCs.
  • Racemic chain mechanism mediated by thiolate nucleophiles.

Conclusions:

  • Cascade cyclizations of alpha, beta-unsaturated thioesters can proceed through distinct enantioselective and racemic pathways.
  • Amidine-based catalysts (ABCs) enable enantioselective acyl transfer.
  • Thiolate nucleophiles mediate a racemic chain mechanism.
  • These findings expand the scope and mechanistic understanding of thioester cyclizations.