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Asymmetric Alkyne Transformation via Gold/Organo Synergistic Catalysis
Ming Bao1, Minghan Yao2, Xinfang Xu1
1School of Chemistry and Chemical Engineering, State Key Laboratory of Bio-Based Fiber Materials, Zhejiang Sci-Tech University, Hangzhou 310014, China.
Accounts of Chemical Research
|April 10, 2026
Summary
This study introduces a synergistic gold/organo catalysis strategy for creating complex chiral molecules from alkynes. This modular approach uses readily available catalysts to achieve high enantioselectivity in challenging alkyne functionalization reactions.
Area of Science:
- Organic Chemistry
- Catalysis
- Asymmetric Synthesis
Background:
- Gold-catalyzed alkyne transformations are powerful for synthesizing chiral molecules but struggle with enantioselectivity.
- Controlling stereochemistry in multi-π bond cleavage is complex due to catalyst dissociation and substrate variability.
- A modular and practical strategy using accessible catalysts for high enantioselectivity is highly desirable.
Purpose of the Study:
- To develop a synergistic gold/organo catalysis strategy to overcome enantioselectivity challenges in alkyne functionalization.
- To enable the construction of polyfunctionalized chiral molecules with high atom economy and bond-forming efficiency.
- To provide a modular and practical platform for novel asymmetric alkyne transformations.
Main Methods:
- Utilized gold-catalyzed generation of gold carbenes from alkynes, followed by chiral Brønsted acid-promoted enantioselective Mannich addition of gold enolates.
- Achieved asymmetric geminal dialkylation of gold carbene species from unactivated internal alkynes.
- Employed chiral quinine-derived squaramide (QN-SQA) cocatalysts for asymmetric ene-type reactions with allylic gold species.
Main Results:
- Successfully synthesized chiral dihydrofuran-3-ones and chiral α-alkoxy-β-amino ketone derivatives.
- Generated polyfunctionalized chiral ketones with quaternary stereocenters via asymmetric geminal dialkylation.
- Demonstrated high enantioselectivity in various asymmetric ene-type reactions (aldol, Mannich, Michael, annulation, amination) using the synergistic approach.
Conclusions:
- The synergistic gold/organo catalysis strategy provides a modular and practical solution for challenging asymmetric alkyne functionalizations.
- This approach circumvents the need for complex chiral ligands by combining achiral gold complexes with readily available chiral organocatalysts.
- The developed flexible platform offers new avenues for asymmetric synthesis and solves long-standing stereochemical problems in alkyne chemistry.
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