α-Cyclodextrin Encapsulation of Bicyclo[1.1.1]pentane Derivatives: A Storable Feedstock for Preparation of [1.1.1]Propellane.

• 影响指数: 16.823
• 发表时间: 02 2021 1
• 来源期刊: Angew Chem Int Ed Engl
• DOI: 10.1002/anie.202014997
• PMID: 33205884
• 文章类型: Journal Article
• 作者列表: Matsunaga T,Kanazawa J,Ichikawa T,Harada M,Nishiyama Y,Duong NT,Matsumoto T,Miyamoto K,Uchiyama M

关键词: [1.1.1]propellane; bicyclo[1.1.1]pentane; deiodination; on-demand preparation; α-cyclodextrin

Abstract

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.