Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.
Chem Commun (Camb). 2019 Feb 19;55(16):2368-2371. doi: 10.1039/c9cc00378a.
Synthesis of the valuable unsymmetric 1,8-dicarbonyl compounds remains underexplored currently. Herein, we disclose a new strategy for the synthesis of 1,8-diketones through the coupling of cyclopropanols and cyanohydrins under visible-light irradiation. The protocol features a cascade of intriguing ring opening of cyclopropanols and remote cyano migration. The unfavorable addition of an alkyl radical to an electron-rich alkene is facilitated by the intramolecular cyanohydrin interception. A variety of multiply functionalized 1,8-diketones are furnished in useful yields. The products could be further transformed into other valuable compounds, manifesting the utility of this method.
目前，有价值的不对称 1,8-二羰基化合物的合成仍未得到充分探索。在此，我们公开了一种通过在可见光照射下环丙醇和氰醇偶联来合成 1,8-二酮的新策略。该方案具有一系列有趣的环丙醇开环和远程氰基迁移反应。通过分子内氰醇的拦截，促进了烷基自由基与富电子烯烃的不利加成。多种多功能化的 1,8-二酮以有用的产率得到。这些产物可以进一步转化为其他有价值的化合物，显示了该方法的实用性。
