Stereoselective Synthesis of Donor−Acceptor Substituted Cyclopropafuranones by Intramolecular Cyclopropanation of Vinylogous Carbonates: Divergent Synthesis of Tetrahydrofuran-3-one, Tetrahydropyran-3-one, and Lactones

A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbonate with carbenes using copper catalyst is described. Each of the cyclopropane bonds of these two acceptor substituted cyclopropafuranones can be cleaved with complete regiocontrol by judicious choice of reaction conditions, leading to a diverse array of frameworks such as tetrahydrofuran-3-one, tetrahydropyran-3-one, and lactones.

本研究报道了一种全新的高立体选择性铜催化卡宾与插烯碳酸酯的分子内环丙烷化反应。两类受体取代环丙烷呋喃酮的每一条环丙烷键，均可通过合理调控反应条件实现完全区域选择性断裂，进而得到四氢呋喃-3-酮、四氢吡喃-3-酮及内酯等多种多样化骨架结构。