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Updated: Aug 3, 2025
12:27
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
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Biomimetic chlorine-induced polyene cyclizations harnessing hypervalent chloroiodane-HFIP assemblies
Julia Binder1,2, Aniruddha Biswas1, Tanja Gulder1,2
1Institute of Chemistry and Mineralogy, Leipzig University Johannisallee 29 04103 Leipzig Germany tanja.gulder@uni-leipzig.de.
Chemical Science
|April 10, 2023
Summary
This study introduces a novel method for chlorination-induced polyene cyclization, overcoming challenges in previous chlorocyclization research. The new technique achieves excellent selectivity, even for complex terpene structures.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Bromo- and iodocyclizations are established synthetic methods.
- Chlorocyclizations remain underdeveloped and challenging in organic synthesis.
- Terpene cyclases are natural enzymes that catalyze complex cyclization reactions.
Purpose of the Study:
- To develop a selective and broadly applicable method for chlorination-induced polyene cyclization.
- To mimic the function of terpene cyclases using synthetic reagents.
- To expand the scope of chlorocyclization reactions to diverse alkene substrates and complex natural product frameworks.
Main Methods:
- Utilizing novel HFIP-chloroiodane networks as reagents.
- Investigating the reaction mechanism of chlorination-induced polyene cyclization.
- Testing the method with a variety of alkenes, including structurally complex terpenes and terpenoids.
Main Results:
- Achieved highly selective chlorination-induced polyene cyclizations (up to d.r. >95:5).
- Demonstrated the general applicability of the developed method across different alkene substrates.
- Successfully applied the cyclization platform to challenging terpene and terpenoid carbon frameworks.
Conclusions:
- The developed HFIP-chloroiodane system provides an effective strategy for challenging chlorocyclizations.
- This method offers a new tool for the synthesis of complex chlorinated organic molecules.
- The approach successfully mimics enzymatic terpene cyclization, opening new avenues in synthetic chemistry.
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