Tan Xiangyu, Gu Qianqian, Yang Xingjiang, Yang Yingying, Hu Bingwei, Mao Shuai, Lin Jun, Jin Yi
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, and School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China.
Department of Medicinal Chemistry, School of Pharmacy, Xi'an Jiaotong University, Xi'an 710061, China.
Org Lett. 2022 Jun 24;24(24):4383-4388. doi: 10.1021/acs.orglett.2c01605. Epub 2022 Jun 13.
Herein, we describe a Pd-catalyzed [2+3] cycloaddition/cross-coupling reaction of allenyl acetates for the selective and diastereoselective synthesis of dendralene-functionalized dihydrofurans. Remarkably, mechanistic studies show the formation of an epoxide from a carbonyl bond via cycloaddition, which is practically and mechanistically significant for the construction of other bioactive heterocyclic epoxides. This research also revealed the utility and potential of allenic esters as C2 synthons and 1,2-biselectrophiles in cycloaddition reactions.
在此，我们描述了一种钯催化的乙酸烯丙酯的[2+3]环加成/交叉偶联反应，用于选择性和非对映选择性地合成具有联烯功能化的二氢呋喃。值得注意的是，机理研究表明通过环加成由羰基键形成环氧化物，这对于构建其他生物活性杂环环氧化物在实际应用和机理方面都具有重要意义。这项研究还揭示了烯丙基酯作为环加成反应中的C2合成子和1,2-双亲电试剂的实用性和潜力。
