Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology , Tianjin University , Tianjin 300072 , China.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072 , China.
J Org Chem. 2019 Aug 16;84(16):10402-10411. doi: 10.1021/acs.joc.9b01601. Epub 2019 Aug 2.
A general and efficient lactonization method of readily available 2-alkynylbenzoates affording biologically important isochromenones has been realized via a solely BF·EtO-mediated 6-endo-dig cyclization process under mild conditions. An alternative mechanistic pathway in which BF·EtO activates the carbonyl of the ester moiety, rather than the alkyne triple bond, was postulated on the basis of control experiment results. Gram-scale reaction and further application for the assembly of more complex molecules demonstrated the practicability of the protocol.
一种通用且高效的内酯化方法，可通过 BF·EtO 介导的温和条件下的 6-endo-dig 环化过程，从易得的 2-炔基苯甲酸酯得到具有重要生物学意义的异色满酮。根据控制实验结果，提出了一种替代的反应机理，其中 BF·EtO 激活酯基的羰基，而不是炔键三键。克级反应和进一步用于组装更复杂分子的应用证明了该方案的实用性。
