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Related Concept Videos

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

2.8K
The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
2.8K
Intramolecular Aldol Reaction01:18

Intramolecular Aldol Reaction

3.1K
Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more than one nucleophilic ⍺ carbon for the base to deprotonate and form the enolates. For example, in symmetrical diketones, there are four ⍺ carbons. Hence, four types of enolates are possible when treated with a base. However, since the molecule is symmetrical, the enolates formed on either side of one carbonyl group are equivalent to those...
3.1K
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

6.3K
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
6.3K
Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

4.6K
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
4.6K
Crossed Aldol Reaction Using Weak Bases01:14

Crossed Aldol Reaction Using Weak Bases

2.7K
This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
2.7K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

3.3K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
3.3K

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Related Experiment Video

Updated: Feb 11, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.9K

syn-Selective Kobayashi aldol reaction using acetals.

Hiroyuki Tsukada1, Yuki Mukaeda, Seijiro Hosokawa

  • 1Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Tokyo 169-8555, Japan.

Organic Letters
|January 22, 2013
PubMed
Summary

Researchers modified the Kobayashi aldol reaction to create syn aldol products. This stereoselective reaction of chiral dienol ethers and acetals is a novel synthetic method for complex molecules.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Stereoselective Synthesis

Background:

  • The Kobayashi aldol reaction is a known method for synthesizing anti-aldol products via remote stereoinduction.
  • Its products possess a polyketide structure, making it valuable for natural product total synthesis.
  • Previous methods primarily focused on anti-aldol product formation.

Purpose of the Study:

  • To explore modifications of the Kobayashi aldol reaction.
  • To investigate the stereoselective synthesis of syn aldol adducts.
  • To develop a novel reaction between chiral dienol ethers and acetals.

Main Methods:

  • Modification of the established Kobayashi aldol reaction conditions.
  • Reaction of chiral dienol ethers with acetals in the presence of a Lewis acid.
  • Analysis of reaction products for stereochemical outcome.

Main Results:

  • The modified reaction successfully yielded syn aldol adducts.
  • High stereoselectivity was achieved in the formation of syn adducts.
  • This represents the first reported stereoselective reaction between chiral dienol ethers and acetals.

Conclusions:

  • A novel stereoselective synthetic route to syn aldol products has been developed.
  • This modification expands the utility of aldol reactions in organic synthesis.
  • The reaction offers a new strategy for constructing complex polyketide-like structures.