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Conjugate Addition of Enolates: Michael Addition

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.

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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).

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...

Amines to Alkenes: Cope Elimination

Amines to Alkenes: Cope Elimination

Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.

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Updated: Aug 12, 2025

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Published on: March 20, 2014

An Organocatalytic Oxy-Cope/Michael Cascade Reaction.

Ryan R G Barrett¹, Donald A Campbell¹, James L Gleason¹

¹Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC H3A 0B8, Canada.

Organic Letters

|January 26, 2023

Summary

Ethyl diazepane carboxylate enables a novel cascade reaction, transforming hexadienes into cyclopentane structures through oxy-Cope rearrangement and Michael addition. This organocatalytic method offers a new pathway for complex molecule synthesis.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

The oxy-Cope rearrangement is a powerful tool for carbon skeleton construction.
Organocatalysis offers sustainable and efficient alternatives to traditional metal catalysis.
Developing cascade reactions that build molecular complexity in a single step is a key goal in synthetic chemistry.

Purpose of the Study:

To develop a novel organocatalytic oxy-Cope rearrangement.
To investigate the use of ethyl diazepane carboxylate in a cascade reaction.
To synthesize cyclopentane-containing compounds from hexadiene precursors.

Main Methods:

Catalysis of the oxy-Cope rearrangement using ethyl diazepane carboxylate.
Activation of substrates via iminium ion formation.
Intramolecular Michael reaction to form cyclopentane rings.
Application to a range of cyclic and acyclic substrates.

Main Results:

Successful catalysis of the oxy-Cope rearrangement and subsequent Michael reaction.
Formation of cyclopentane-containing products from diverse hexadiene precursors.
High stereocontrol observed in ring expansion/cyclopentannulation of fused substrates.
Demonstration of tolerance to vinyl substituent variations.

Conclusions:

Ethyl diazepane carboxylate effectively catalyzes a cascade oxy-Cope rearrangement/Michael addition.
This methodology provides a novel route to complex cyclopentane structures.
The reaction expands the scope of iminium organocatalysis to cascade transformations.