Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University, No. 2 North Cuihu Road, 650091 Kunming, China.
School of Chemistry and Chemical Engineering, and Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 400030, China.
J Am Chem Soc. 2021 Mar 24;143(11):4179-4186. doi: 10.1021/jacs.1c01366. Epub 2021 Mar 16.
We present herein an unprecedented desymmetrization of 1,3-diones by enantioselective intermolecular condensation. Under the catalysis by a chiral phosphoric acid, a range of readily available 1,3-diones undergo reaction with hydrazines to produce cyclic and acyclic keto-hydrazones bearing an all-carbon quaternary center in high efficiency and enantioselectivity. These compounds are also highly versatile for the preparation of multifunctional building blocks and heterocycles in excellent stereoselectivity.
我们在此展示了手性磷酸催化的前所未有的 1,3-二酮的不对称分子间缩合反应。在该催化作用下,一系列易得的 1,3-二酮与腙反应,以高产率和对映选择性得到了含有全碳季碳中心的环状和非环状酮腙。这些化合物也非常适合用于制备多功能砌块和杂环化合物,具有优异的立体选择性。