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Updated: Jun 21, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
B-Alkylcatecholborane-mediated tandem radical conjugated addition-aldol cyclization
Alice Beauseigneur1, Cecilia Ericsson, Philippe Renaud
1Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
This study introduces a novel one-pot method for synthesizing complex molecules. The radical conjugate addition and aldol reaction efficiently create stereochemically rich cyclic compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Stereoselective Synthesis
Background:
- Enones are versatile Michael acceptors in organic synthesis.
- Radical conjugate additions offer unique reactivity pathways.
- Aldol reactions are fundamental carbon-carbon bond-forming reactions.
Purpose of the Study:
- To develop an efficient one-pot procedure combining radical conjugate addition and intramolecular aldol reaction.
- To achieve stereoselective synthesis of monocyclic and bicyclic compounds.
- To explore the construction of molecules with multiple contiguous stereocenters.
Main Methods:
- Utilized B-alkylcatecholboranes for radical conjugate addition to enones.
- Integrated an intramolecular aldol reaction in a sequential one-pot process.
- Applied the methodology to synthesize various monocyclic and bicyclic structures.
Main Results:
- Successfully demonstrated a one-pot procedure for sequential radical conjugate addition-aldol reaction.
- Achieved stereoselective synthesis of complex cyclic products.
- Generated products containing up to four contiguous stereogenic centers.
Conclusions:
- The developed one-pot strategy is effective for constructing stereochemically dense cyclic molecules.
- This method provides a powerful tool for accessing complex organic structures.
- The approach offers advantages in efficiency and stereocontrol for synthetic chemists.
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