The Alkyne Zipper Reaction: A Useful Tool in Synthetic Chemistry
Abstract
:1. Introduction
2. The Alkyne Zipper Reaction Mechanism
3. The Alkyne Zipper Reaction in Synthesis
3.1. Pheromones and Long Chained Alcohols
3.2. Fatty Acids and Derived Structures
3.3. Macrocycles
3.4. Other Natural Product Classes
3.5. Noyori Reduction/Acetylene Zipper Combination
3.6. Probes via Copper Catalyzed Azide–Alkyne Cycloaddition (Click Chemistry)
3.7. Synthesis of Arylalkadiynols via an Acetylene Zipper-Sonogashira Reaction Sequence
3.8. Polyurethane Materials
4. Conclusions and Future Perspectives
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Abbreviations
APA | 1,3-Diaminopropane |
CTAB | Cetyltrimethylammonium bromide |
CuAAC | Copper catalyzed azide–alkyne cycloaddition |
DCM | Dichloromethane |
DMF | Dimethylformamide |
DMSO | Dimethyl sulfoxide |
DSF | Diffusible signal factor |
HMPA | Hexamethylphosphoramide |
KAPA/PAPA | Potassium 3-aminopropylamide |
KOt-Bu | Potassium tert-butoxide |
LAETA | Lithium 2-aminoethylamide |
MOM | Methoxymethyl |
NaAPA | Sodium 3-aminopropylamide |
PU | Polyurethane |
rt | Room temperature |
SDS-PAGE | Sodium dodecyl sulfate–polyacrylamide gel electrophoresis |
TAMRA-N3 | Tetramethylrhodamine azide |
TBAI | Tetrabutylammonium iodide |
TBDPS | tert-Butyldiphenylsilyl |
THF | Tetrahydrofuran |
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Sørskår, Å.M.; Stenstrøm, H.Ø.K.; Stenstrøm, Y.; Antonsen, S.G. The Alkyne Zipper Reaction: A Useful Tool in Synthetic Chemistry. Reactions 2023, 4, 26-65. https://doi.org/10.3390/reactions4010002
Sørskår ÅM, Stenstrøm HØK, Stenstrøm Y, Antonsen SG. The Alkyne Zipper Reaction: A Useful Tool in Synthetic Chemistry. Reactions. 2023; 4(1):26-65. https://doi.org/10.3390/reactions4010002
Chicago/Turabian StyleSørskår, Åshild Moi, Helge Ø. K. Stenstrøm, Yngve Stenstrøm, and Simen Gjelseth Antonsen. 2023. "The Alkyne Zipper Reaction: A Useful Tool in Synthetic Chemistry" Reactions 4, no. 1: 26-65. https://doi.org/10.3390/reactions4010002