Construction of spirocyclic oxindole derivatives by copper-catalyzed enantioselective Michael/hemiketalization in aqueous media.

Chem Commun (Camb)

Hefei National Research center for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences, Collaborative Innovation Center of Suzhou Nano Science and Technology & School of Chemistry and Materials Science in University of Science and Technology of China, Hefei, 230026, P. R. China.

Published: September 2022

An asymmetric Michael/hemiketalization reaction between isatin-derived β,γ-unsaturated α-ketoesters and 4-hydroxycoumarins was developed in aqueous media. A series of chiral spirooxindole derivatives with an all-carbon quaternary stereogenic center were obtained in high yields (up to 93%) and excellent enantioselectivities (up to 98%).

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http://dx.doi.org/10.1039/d2cc04370jDOI Listing

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