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Related Concept Videos

Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the strong interaction...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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Related Experiment Video

Updated: Jul 5, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

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Published on: February 16, 2018

Enantioselective Radical Cascade Cyclization to Axially Chiral Medium-Sized Lactones.

Yudong Hao1,2, Jicai Chen1, Naifeng Hu1

  • 1College of Chemistry, State Key Laboratory of Antiviral Drugs and Pingyuan Laboratory, Zhengzhou University, Zhengzhou, Henan, P. R. China.

Angewandte Chemie (International Ed. in English)
|July 3, 2026
PubMed
Summary

This study introduces a novel photoredox/copper-catalyzed method for synthesizing chiral lactones using radical cascade cyclization. The efficient enantioselective approach offers a new pathway for creating complex molecules with high stereocontrol.

Keywords:
axial chiralitycopper catalysismedium‐sized ringsphotoredox catalysisradical cascade cyclization

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Stereoselective Synthesis

Background:

  • Conventional methods for synthesizing axially chiral medium-sized lactones often require strict reaction conditions and prefunctionalized substrates.
  • Radical chemistry offers an alternative but achieving high enantioselectivity remains challenging.

Purpose of the Study:

  • To develop a synergistic photoredox/copper-catalyzed radical cascade cyclization for the enantioselective synthesis of axially chiral medium-sized lactones.
  • To utilize alkyl halides as radical precursors for a more versatile synthetic strategy.

Main Methods:

  • Employing a photoredox catalyst and a chiral copper complex for a synergistic catalytic system.
  • Generating radicals from alkyl halides via single electron transfer (SET) initiated by photoredox catalysis.
  • Facilitating radical addition to non-polarized alkenes followed by intramolecular C-O bond formation.

Main Results:

  • Achieved high yields (up to 83%) and excellent enantioselectivity (up to 96% e.e.) with high diastereomeric ratios (>20:1 d.r.).
  • Demonstrated synthetic utility through late-stage diversification of bioactive molecules.
  • Theoretical calculations identified C-O bond formation as the stereodetermining step.

Conclusions:

  • The developed method provides an efficient and stereoselective route to axially chiral medium-sized lactones.
  • The strategy overcomes limitations of traditional ionic pathways by using readily available alkyl halides.
  • A central-to-axial chirality relay mechanism governs the stability of the chiral scaffold.