Xu Ting, Chen Ke, Zhu Hong-Yu, Hao Wen-Juan, Tu Shu-Jiang, Jiang Bo
School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P.R. China.
Org Lett. 2020 Mar 20;22(6):2414-2418. doi: 10.1021/acs.orglett.0c00613. Epub 2020 Mar 9.
A new Lewis acid catalyzed alkyne-carbonyl metathesis/oxa-Michael addition relay was first reported, leading to the atom-economic synthesis of unreported functionalized indolone-containing naphtho[2,1-]furan-1-ones with a quaternary center in good to excellent yields and high diastereoselectivity through scission/recombination of C-O double bonds under the mild conditions. A Yb(OTf)-catalyzed reaction between α-alkynyl naphthalen-2-ols and isatins worked efficiently and offered a convergent and regioselective protocol to construct cyclic ketones via alkyne polyfunctionalization.
首次报道了一种新型路易斯酸催化的炔-羰基复分解/氧杂-迈克尔加成接力反应，该反应在温和条件下通过C-O双键的断裂/重组，以良好至优异的产率和高非对映选择性实现了原子经济性合成未报道的含官能团化吲哚酮的萘并[2,1-]呋喃-1-酮，且带有一个季碳中心。Yb(OTf)催化的α-炔基萘-2-醇与异吲哚酮之间的反应高效进行，提供了一种通过炔烃多官能化构建环状酮的汇聚性和区域选择性方法。
