Shah Babar Hussain, Khan Sardaraz, Zhao Can, Zhang Yong Jian
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, and School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China.
Sichuan Research Institute, Shanghai Jiao Tong University, Chengdu 610042, P. R. China.
J Org Chem. 2023 Aug 18;88(16):12100-12104. doi: 10.1021/acs.joc.3c00976. Epub 2023 Aug 8.
An efficient method for the enantioselective synthesis of 2,3-dihydrofurans bearing a quaternary stereocenter has been developed via Pd-catalyzed asymmetric allylic cycloaddition and a retro-Dieckmann Fragmentation cascade. The asymmetric allylic cycloaddition of vinylethylene carbonates with 3-cyanochromone followed by base-assisted retro-Dieckmann fragmentation proceeded smoothly via a one-pot process to produce chiral 3,4-disubstituted 2,3-dihydrofurans in high yields with excellent enantioselectivities.
通过钯催化的不对称烯丙基环加成反应和逆迪克曼碎片化串联反应，开发了一种对映选择性合成带有季碳立体中心的2,3-二氢呋喃的有效方法。碳酸乙烯酯与3-氰基色酮的不对称烯丙基环加成反应，随后在碱辅助下进行逆迪克曼碎片化反应，通过一锅法顺利进行，以高产率和优异的对映选择性生成手性3,4-二取代的2,3-二氢呋喃。
