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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Stereoisomerism02:52

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Diastereoselective imine-bond formation through complementary double-helix formation.

Hidekazu Yamada1, Yoshio Furusho, Eiji Yashima

  • 1Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.

Journal of the American Chemical Society
|April 18, 2012
PubMed
Summary

Chiral amidine templates guide the diastereoselective formation of double-helix imine bonds from achiral monomers. This templating strategy controls the stereochemistry of the resulting racemic amine, influencing reaction rates and selectivity.

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Area of Science:

  • Supramolecular chemistry
  • Organic synthesis
  • Stereochemistry

Background:

  • Chiral templates are crucial for controlling stereoselective reactions.
  • Amidine dimers offer a versatile platform for constructing complex molecular architectures.
  • Imine bond formation is a fundamental reaction in organic chemistry.

Purpose of the Study:

  • To synthesize optically active amidine dimer strands as templates.
  • To investigate their use in diastereoselective imine-bond formation.
  • To understand the influence of template structure on stereochemical outcomes.

Main Methods:

  • Synthesis of chiral and achiral amidine dimer strands with varied linkers.
  • Diastereoselective imine formation using achiral carboxylic acid monomers and racemic 1,2-cyclohexanediamine.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Kinetic studies to elucidate reaction mechanisms.

Main Results:

  • Amidine dimer templates successfully directed the diastereoselective formation of preferred-handed double helices.
  • Template chirality and linker rigidity significantly impacted the diastereoselectivity of the racemic amine.
  • Imine bond formation proceeds via a two-step reversible mechanism, with the second step being rate-determining and helix-forming.

Conclusions:

  • Optically active amidine dimers serve as effective chiral templates for diastereoselective imine synthesis.
  • The supramolecular structure of the template dictates the stereochemical preference of the product.
  • This work provides insights into template-controlled synthesis and the mechanism of helical self-assembly.