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Related Concept Videos

Conjugate Addition of Enolates: Michael Addition01:08

Conjugate Addition of Enolates: Michael Addition

The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

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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).
Cycloaddition Reactions: Overview01:16

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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.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Published on: May 21, 2019

Enantioselective copper-catalyzed reductive Michael cyclizations.

Claire L Oswald1, Justine A Peterson, Hon Wai Lam

  • 1School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom.

Organic Letters
|October 9, 2009
PubMed
Summary

Chiral copper catalysts enable highly enantioselective reductive Michael cyclizations using siloxanes. The choice of biaryl- or ferrocene-based chiral bisphosphines dictates the diastereochemical outcome of these important organic reactions.

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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Reductive Michael cyclizations are crucial carbon-carbon bond-forming reactions.
  • Developing enantioselective methods for these transformations is a significant challenge in organic synthesis.

Purpose of the Study:

  • To investigate the use of chiral copper-bisphosphine complexes for highly enantioselective reductive Michael cyclizations.
  • To explore the influence of different chiral bisphosphine ligands on the diastereochemical outcome.

Main Methods:

  • Catalytic asymmetric synthesis employing chiral copper-bisphosphine complexes.
  • Utilizing siloxanes as stoichiometric reductants.
  • Reaction of substrates with two alpha,beta-unsaturated carbonyl moieties.

Main Results:

  • Achieved highly enantioselective reductive Michael cyclizations.
  • Demonstrated that the diastereochemical outcome is dependent on the type of chiral bisphosphine ligand used (biaryl- vs. ferrocene-based).

Conclusions:

  • Chiral copper-bisphosphine complexes are effective catalysts for enantioselective reductive Michael cyclizations.
  • Ligand structure plays a critical role in controlling diastereoselectivity, offering a pathway for tailored synthesis.