Developments in the construction of cyclopropanols
Qiang Liu1, Bingxin You, Guanqun Xie
1School of Materials Science and Engineering, Dongguan University of Technology, Dongguan, 523808, China. wangxx@dgut.edu.cn.
Organic & Biomolecular Chemistry
|December 4, 2019
Summary
This review summarizes cyclopropanol synthesis, a key step for creating complex molecules via ring-opening and cross-coupling reactions. Improved methods offer new substrates for diverse applications.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Ring-opening of cyclopropanols is a vital reaction for synthesizing complex organic molecules.
- This reaction enables facile synthesis of multifunctional compounds through coupling with various partners.
- Access to diverse cyclopropanol substrates is crucial for cascade reactions, but their synthesis has been underdeveloped.
Purpose of the Study:
- To summarize recent advancements in cyclopropanol formation.
- To introduce new, stereoselective methods for producing cyclopropanol substrates.
- To present improved syntheses of known cyclopropanols.
Main Methods:
- Literature review of cyclopropanol synthesis.
- Development of highly stereoselective cyclopropanol production methods.
- Optimization of existing cyclopropanol synthesis routes.
Main Results:
- A comprehensive overview of recent cyclopropanol formation strategies.
- Introduction of novel, stereoselective cyclopropanol precursors.
- Demonstration of improved synthetic routes for established cyclopropanols.
Conclusions:
- The review facilitates broader applications of cyclopropanol ring-opening/coupling reactions.
- New substrates and improved syntheses will advance the creation of pharmaceuticals, natural products, and organic intermediates.
- Further research into cyclopropanol construction is essential for synthetic chemistry.
More Related Videos
Related Concept Videos
Cycloaddition Reactions: Overview
3.3K
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.
3.3K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.7K
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).
2.7K
Conformations of Cycloalkanes
13.9K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3 hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
13.9K
Stability of Substituted Cyclohexanes
14.6K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
14.6K
Cycloalkanes
15.1K
Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
15.1K
Cycloaddition Reactions: MO Requirements for Thermal Activation
4.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.1K


