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DOI: 10.1055/s-0037-1610290
Highly Diastereo-, α-Regioselective Catalyst-Free Construction of Adjacent Dispirobisoxindoles with Three Contiguous Quaternary Carbon Centers
We are grateful for the financial support from the National Natural Science Foundations of China (No. 81560563, No. 81760625, and No. 21402132); Project of Guizhou province (Qian Ke He Zi [2016]5623, Qian Ke He Zi [2017]5609, Qian Ke He G Z [2015]4001, and Qian Jiao Yan He JG Zi [2016]06).Publication History
Received: 21 July 2018
Accepted after revision: 31 August 2018
Publication Date:
24 September 2018 (online)


§ These two authors contributed equally to this work
Abstract
A new methodology was developed for the highly diastereoselective construction of dispirobisoxindole scaffolds via a domino α-regioselective Michael/cyclization reaction sequence of 3-isothiocyanato oxindoles and isatylidene malononitriles under catalyst-free conditions. Complex polycyclic oxindoles featuring two side-by-side oxindole skeletons and three contiguous quaternary carbon centers were synthesized in up to 95% yield and >20:1 dr. This protocol could provide libraries of stereochemically rich small molecules that will help in the search for new bioactive molecules.
Key words
3-isothiocyanato oxindoles - quaternary carbon center - diastereoselective - α-regioselective - catalyst-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610290.
- Supporting Information