α-Cyclodextrin Encapsulation of Bicyclo[1.1.1]pentane Derivatives: A Storable Feedstock for Preparation of [1.1.1]Propellane
| Autor: | Yusuke Nishiyama, Masanobu Uchiyama, Tomohiro Ichikawa, Kazunori Miyamoto, Takashi Matsumoto, Mei Harada, Nghia Tuan Duong, Tadafumi Matsunaga, Junichiro Kanazawa |
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| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Cyclodextrin Bicyclic molecule 010405 organic chemistry Chemistry General Medicine General Chemistry Raw material 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Encapsulation (networking) Pentane Propellane chemistry.chemical_compound Organic chemistry |
| Zdroj: | Angewandte Chemie (International ed. in English). 60(5) |
| ISSN: | 1521-3773 |
| Popis: | The bicyclo[1.1.1]pentane (BCP) scaffold is useful in medicinal chemistry, and many protocols are available for synthesizing BCP derivatives from [1.1.1]propellane. However, little progress has been made in the preparation of [1.1.1]propellane since the first practical synthesis in 1985. Here, we report the α-cyclodextrin (α-CD) encapsulation of BCP derivatives, affording a stable, readily storable material from which BCPs can be easily and quantitatively recovered. We have also developed new and simple protocols for deiodination reaction of 1,3-diiodo BCP to afford [1.1.1]propellane in protic/aprotic/polar/non-polar solvents. The combination of these methodologies enables simple, on-demand preparation of [1.1.1]propellane in various solvents under mild conditions from α-CD capsules containing 1,3-diiodo BCP. |
| Databáze: | OpenAIRE |
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