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α‐Cyclodextrin Encapsulation of Bicyclo[1.1.1]pentane Derivatives: A Storable Feedstock for Preparation of [1.1.1]Propellane
Author(s) -
Matsunaga Tadafumi,
Kanazawa Junichiro,
Ichikawa Tomohiro,
Harada Mei,
Nishiyama Yusuke,
Duong Nghia Tuan,
Matsumoto Takashi,
Miyamoto Kazunori,
Uchiyama Masanobu
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202014997
Subject(s) - propellane , chemistry , bicyclic molecule , pentane , raw material , combinatorial chemistry , organic chemistry , cyclodextrin , computational chemistry
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. Here, we report (1) the α‐cyclodextrin (α‐CD) encapsulation of BCP derivatives, affording a stable, readily storable material from which BCPs can be easily and quantitatively recovered and (2) 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.