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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Factors Affecting α-Alkylation of Ketones: Choice of Base01:10

Factors Affecting α-Alkylation of Ketones: Choice of Base

α-Alkylation of ketones is achieved in the presence of alkyl halides and a base. The reaction proceeds via the formation of an enolate ion followed by nucleophilic substitution. The choice of base employed is essential as it is the key factor in determining the reaction outcome.
The reaction involving bases like EtO− whose conjugate acid EtOH (pKa = 15.9) is stronger than the ketone (pKa = 19.2) results in an equilibrium mixture with higher ketone concentration. As a consequence, side reactions...
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
When dissolved in liquid ammonia, an alkali metal, such as sodium, dissociates into a...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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Synthesizing Amino Acids Modified with Reactive Carbonyls in Silico to Assess Structural Effects Using Molecular Dynamics Simulations
05:57

Synthesizing Amino Acids Modified with Reactive Carbonyls in Silico to Assess Structural Effects Using Molecular Dynamics Simulations

Published on: April 26, 2024

The SAMP alkylation: a computational study.

Rainer Koch1

  • 1Institut für Reine und Angewandte Chemie and Center of Interface Science, Carl von Ossietzky Universität Oldenburg, P.O. Box 2503, 26111, Oldenburg, Germany. rainer.koch@uni-oldenburg.de

Organic & Biomolecular Chemistry
|March 5, 2011
PubMed
Summary
This summary is machine-generated.

This study computationally evaluates the SAMP alkylation mechanism for stereoselective C-C bond formation. It reveals the key intermediate structure and explains selectivity through transition state stabilization, aiding synthetic method development.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Reaction Mechanism

Background:

  • The SAMP alkylation is a key reaction for stereoselective C-C bond formation.
  • A previously proposed S(E)2'-front mechanism requires further evaluation with current experimental data.

Purpose of the Study:

  • To computationally evaluate the S(E)2'-front mechanism of the SAMP alkylation.
  • To elucidate the structure of the key intermediate and explain the reaction's metalloretentive nature.
  • To correlate computational findings with experimental enantioselectivity (ee) values.

Main Methods:

  • Utilized semiempirical, density functional, and perturbation theoretical computational methods.
  • Analyzed the structure of the key intermediate in the SAMP alkylation.
  • Calculated activation energy differences for various reaction conditions.

Main Results:

  • Revealed the structure of the key intermediate and explained the metalloretentive aspect of the mechanism.
  • Correlated calculated activation energy differences with experimental enantioselectivity values across different electrophiles and carbonyl sources.
  • Identified electrophile-lithium interactions as the source of internal transition state stabilization, explaining selectivity.

Conclusions:

  • The S(E)2'-front mechanism is supported by computational evidence and explains experimental observations.
  • Computational screening can effectively guide the development of the SAMP alkylation synthetic method.
  • The study provides a deeper understanding of stereoselective C-C bond formation.