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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

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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).
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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.
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Updated: May 31, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Asymmetric Reductive Three-Component Annulation Reaction for Constructing Fused N-Heterocycles With Contiguous

Guang-Peng Lu1, Huan-Feng Jiang1, Cheng-Gang Ci2

  • 1Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, P. R. China.

Angewandte Chemie (International Ed. in English)
|May 29, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces an efficient method for synthesizing optically active fused N-heterocycles using a chiral phosphoric acid catalyst. The novel reaction creates complex molecules with high stereoselectivity, valuable for medicinal chemistry.

Keywords:
asymmetric annulation reactionchiral phosphoric acid catalysiscontiguous stereocentersfused N‐heterocycleshydrodearomatization

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Asymmetric Catalysis

Background:

  • Efficient synthesis of optically active fused N-heterocycles is crucial for drug discovery.
  • Hydrodearomative annulation of azaarenes is a challenging but promising synthetic strategy.

Purpose of the Study:

  • To develop a novel reductive three-component reaction for constructing fused N-heterocycles.
  • To achieve high stereoselectivity, including contiguous quaternary and tertiary carbon stereocenters.

Main Methods:

  • Utilized a chiral phosphoric acid and PhSiH3 catalytic system.
  • Employed a three-component reaction involving isoquinolinium salts, formaldehyde, and N-alkyl anilines.
  • Conducted DFT calculations to elucidate the reaction mechanism and stereoselectivity.

Main Results:

  • Successfully synthesized fused N-heterocycles with good isolated yields (up to 88%).
  • Achieved high diastereoselectivities (>20:1 dr) and enantioselectivities (up to 96.5:3.5 er).
  • Identified C-H···O interactions and steric repulsion as key factors in enantioselectivity.

Conclusions:

  • The developed method provides an efficient route to complex, stereochemically rich N-heterocycles.
  • The chiral phosphoric acid catalyst plays a dual role in intermediate formation and stereocontrol.
  • This approach offers significant potential for advancing medicinal chemistry applications.