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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
Prochirality02:05

Prochirality

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...
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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Seebach's conjunctive reagent enables double cyclizations.

Brent D Chandler1, Jason T Roland, Yukai Li

  • 1Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, New Jersey 08544, USA.

Organic Letters
|May 21, 2010
PubMed
Summary
This summary is machine-generated.

Direct coupling reactions between ketones and Seebach's nitropropenyl pivaloate reagent efficiently create novel bicyclic ring systems. This chemistry enables the rapid synthesis of densely functionalized and rigid molecular frameworks with cis-ring fusions.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Ketones are versatile carbonyl compounds utilized in various organic transformations.
  • Seebach's nitropropenyl pivaloate reagent offers unique reactivity for carbon-carbon bond formation.

Purpose of the Study:

  • To explore the direct coupling reaction between ketones and Seebach's nitropropenyl pivaloate reagent.
  • To investigate the formation of new ring systems and bonds through this reaction.
  • To develop a method for rapid synthesis of functionalized bicyclic compounds.

Main Methods:

  • Reaction of ketones (flanked by nucleophilic atoms) with Seebach's nitropropenyl pivaloate reagent.
  • Analysis of reaction products to identify new ring systems and bond formations.
  • Characterization of the stereochemistry of ring fusions.

Main Results:

  • Direct coupling reactions yield two new ring systems and three new bonds.
  • Cis-ring fusions are observed in the formation of 5,5-, 5,6-, and 6,6-bicycles.
  • The reaction provides rapid access to densely functionalized and rigid frameworks.

Conclusions:

  • The described chemistry offers an efficient route to complex bicyclic structures.
  • This method facilitates the rapid construction of molecules with defined stereochemistry.
  • The developed synthetic strategy is valuable for creating rigid and functionalized molecular scaffolds.