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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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Preparation of Alcohols via Substitution Reactions01:38

Preparation of Alcohols via Substitution Reactions

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Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group.  The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2,  depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
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Prochirality02:05

Prochirality

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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...
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

18.6K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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Updated: Apr 10, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Stereoselective Synthesis of Tetrasubstituted Axially Chiral N-Vinylquinolinones via Substrate-Directed Asymmetric

Wen-Biao Zhou1, Jie Wang1, Meng-Jie Zhang1

  • 1School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 9, 2026
PubMed
Summary

This study introduces an asymmetric allylic substitution-isomerization (AASI) strategy for synthesizing tetrasubstituted axially chiral N-vinylquinolinones. The precursor structure dictates stereochemical outcomes, enabling selective synthesis of complex chiral molecules.

Keywords:
asymmetric allylic substitutionaxially chiral N‐vinylquinolinonesorganocatalysisstereodivergent synthesisstereospecific isomerization

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Medicinal Chemistry

Background:

  • Axially chiral molecules are crucial scaffolds in medicinal chemistry.
  • Developing efficient synthetic routes to tetrasubstituted N-vinylquinolinones remains a challenge.

Purpose of the Study:

  • To develop a novel asymmetric allylic substitution-isomerization (AASI) strategy.
  • To synthesize tetrasubstituted axially chiral N-vinylquinolinones.
  • To investigate the influence of precursor structure on stereochemical outcomes.

Main Methods:

  • Employing an asymmetric allylic substitution-isomerization (AASI) reaction.
  • Utilizing various methylbenzylidene (MBH) carbonate precursors derived from 2-pyridinecarboxaldehyde.
  • Analyzing the stereochemical outcome based on precursor modifications (e.g., methyl ester vs. tert-butyl group).

Main Results:

  • Achieved high E-selectivity using MBH carbonates with a methyl ester group.
  • Demonstrated a loss of stereocontrol with tert-butyl group substitution, indicating potential for stereodivergent synthesis.
  • Successfully synthesized congested axially chiral scaffolds.

Conclusions:

  • The developed AASI strategy provides a practical and efficient route to axially chiral N-vinylquinolinones.
  • Precursor structure is critical for controlling stereoselectivity in AASI reactions.
  • The findings open avenues for stereodivergent synthesis of complex chiral molecules.