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Conjugate Addition of Enolates: Michael Addition01:08

Conjugate Addition of Enolates: Michael Addition

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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.0K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.8K
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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Related Experiment Video

Updated: Jan 9, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Computational Study on Data Integration in Chiral Catalyst Design: A Case Study Using Michael Addition Reactions.

Shigeru Yamaguchi1

  • 1RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.

The Journal of Organic Chemistry
|December 2, 2025
PubMed
Summary
This summary is machine-generated.

This study integrates 3D structural data from transition states to design chiral catalysts. This data-driven approach improved enantioselectivity across seven distinct catalytic reaction systems.

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Area of Science:

  • Molecular Catalysis
  • Computational Chemistry
  • Data Science

Background:

  • Molecular catalysis often assumes similar structures lead to similar properties.
  • Regression analysis using free energy relationships is common, typically focusing on single scaffold variations.
  • Existing methods often lack comprehensive data integration for complex catalyst design.

Purpose of the Study:

  • To develop a data-driven approach for chiral catalyst design.
  • To leverage integrated datasets of transition-state structures and energy differences for regression analysis.
  • To improve computed enantioselectivity in diverse catalytic systems.

Main Methods:

  • Utilized 718 transition-state (TS) structures computed via density functional theory (DFT).
  • Derived three-dimensional, image-like (voxel) descriptors from TS structures.
  • Performed regression analysis using integrated data across seven reaction types (e.g., organocatalysis, transition-metal catalysis, Michael addition, Diels-Alder).

Main Results:

  • Successfully integrated data from seven distinct reaction systems.
  • Regression models enabled the design of chiral catalysts with enhanced computed enantioselectivity.
  • Achieved improved enantioselectivity in all seven tested catalytic systems.

Conclusions:

  • Data integration of 3D TS descriptors and energy data is effective for chiral catalyst design.
  • The developed methodology offers a powerful tool for accelerating catalyst discovery.
  • A web platform (https://mcds.riken.jp) is available for accessing data and design tools.