Boroxine template for macrocyclization and postfunctionalization
Boroxine template for macrocyclization and postfunctionalization
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用于大环化和后官能化的硼氧烷模板
DOI：
10.1039/d2cc04691a
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发表时间：
2022
影响因子：
4.9
通讯作者：
Hidetoshi Kawai
中科院分区：
文献类型：
--
作者：
Kosuke Ono;Satoru Onodera;Hidetoshi Kawai
提出了一种利用硼砂生成大环分子的新合成策略。为此，由相应的硼酸底物脱水形成的具有不同长度烯基链的3,5-二（烯氧基）苯硼氧酮分子内三次烯烃复分解，并与品纳醇一起处理，用于生产具有三个硼酸单位的39-，45-和51-元的大环化合物。硼氧基部分作为共价模板，但也可用于后修饰大环。以这种方式实现的硼罗辛模板大环化不需要添加模板分子，简化了合成过程。
A novel synthetic strategy for large macrocyclic molecules using boroxine formation was developed. For this, the threefold intramolecular olefin metathesis of 3,5-bis(alkenyloxy)phenylboroxines with various lengths of alkenyl chains, formed by the dehydration of the corresponding boronic acid substrates, together with treatment with pinacol, was used to produce 39-, 45-, and 51-membered macrocyclic compounds with three boronate units. The boroxine moiety functions as a covalent template but can also be used to postmodify the macrocycle. Boroxine-templated macrocyclization implemented in this way does not require the addition of template molecules and simplifies the synthetic procedure.