Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
State Key Laboratory of Synthetic Chemistry and Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. China.
Org Lett. 2020 Jun 5;22(11):4306-4310. doi: 10.1021/acs.orglett.0c01357. Epub 2020 May 22.
A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl -quinone methide (-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular -Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.
DBU 催化的炔丙胺和水一锅串联反应已被开发用于合成黄烷酮。该过程通过水对炔基-醌甲醚（-AQM）的 1,4-共轭加成、随后的炔烃-丙二烯异构化和随后的分子内迈克尔加成进行。该策略提供了一种方便的方法，以良好至优异的收率获得广泛的黄烷酮，具有良好的官能团耐受性，特别是反应性卤官能团。
