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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.

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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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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...

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Enantioselective synthesis of 1,2-disubstituted thiocyclobutanes via Michael addition.

Emma G L Robert¹, Jerome Waser¹

¹Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne 1015 Lausanne Switzerland jerome.waser@epfl.ch.

Chemical Science

|June 9, 2025

Summary

This summary is machine-generated.

Researchers developed a new method for synthesizing thio-substituted cyclobutanes using sulfa-Michael addition. This approach achieves high yields and stereoselectivity, offering a valuable tool for organic synthesis.

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Published on: February 7, 2019

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Cyclobutanes are important structural motifs in medicinal chemistry.
Efficient synthesis of functionalized cyclobutanes remains a challenge.

Purpose of the Study:

To develop a diastereoselective and enantioselective synthesis of thio-substituted cyclobutanes.
To explore the utility of sulfa-Michael addition with cyclobutenes.

Main Methods:

Sulfa-Michael addition reaction using cyclobutenes.
Employing DBU as a base catalyst for achiral synthesis.
Utilizing a chiral bifunctional acid-base catalyst for asymmetric synthesis.

Main Results:

Achieved up to quantitative yields of thio-cyclobutane esters and amides with >95:5 diastereomeric ratio (dr).
Obtained thio-cyclobutanes with high enantioselectivity (up to 99.7:0.3 enantiomeric ratio, er) using a chiral catalyst.

Conclusions:

The developed method provides efficient access to stereodefined thio-substituted cyclobutanes.
The chiral catalyst enables highly enantioselective synthesis, expanding synthetic possibilities.