α‐Cyclodextrin Encapsulation of Bicyclo[1.1.1]pentane Derivatives: A Storable Feedstock for Preparation of [1.1.1]Propellane
α‐Cyclodextrin Encapsulation of Bicyclo[1.1.1]pentane Derivatives: A Storable Feedstock for Preparation of [1.1.1]Propellane
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双环[1.1.1]戊烷衍生物的α-环糊精封装：用于制备[1.1.1]丙烷的可储存原料
DOI：
10.1002/anie.202014997
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发表时间：
2021
期刊：
影响因子：
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通讯作者：
Uchiyama Masanobu
中科院分区：
文献类型：
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作者：
Matsunaga Tadafumi;Kanazawa Junichiro;Ichikawa Tomohiro;Harada Mei;Nishiyama Yusuke;Duong Nghia Tuan;Matsumoto Takashi;Miyamoto Kazunori;Uchiyama Masanobu
双环[1.1.1]戊烷(BCP)支架在药物化学中有很大的应用价值，从[1.1.1]螺旋烷合成双环[1.1.1]戊烷(BCP)衍生物的方法有很多。在这里，我们报道(1) α-环糊精(α-CD)包埋BCP衍生物，提供了一种稳定的、易于储存的材料，从其中可以容易地和定量地回收BCP；(2) 新的和简单的方法用于1，3-二碘BCP的脱碘反应，得到在质子/非质子/极性/非极性溶剂中的[1.1.1]丙烷。结合这些方法，可以在温和的条件下，在各种溶剂中从含有1，3-二碘BCP的α-CD胶囊中按需简单地制备[1.1.1]螺旋桨。
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.