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DOI: 10.1055/s-0037-1610875
Highly Efficient, Catalyst-Free, Diastereoselective, Diversity-Oriented Synthesis of Dihydrocoumarin–Pyrrolidine–Spirooxindoles Bearing Three Contiguous Stereocenters
We are grateful for the financial support from the National Natural Science Foundation of China (No. 81660576, No. 81560563, No. 81760625) and the Projects of Guizhou Province (Qian Ke He Zi [2016]5623, [2018]5670, [2017]5609 and Qian Jiao Yan He JG Zi [2016]06).Publication History
Received: 21 December 2018
Accepted after revision: 08 March 2019
Publication Date:
03 April 2019 (online)
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Abstract
A new methodology has been developed for the highly efficient diastereoselective construction of dihydrocoumarin–pyrrolidine–spirooxindole collections via a domino Michael/annulation reaction of 3-isothiocyanato oxindoles and coumarins under catalyst-free conditions. The resulting biologically important molecules bearing three pharmacophores and three contiguous stereocenters were obtained in up to 92% yield and >20:1 dr. It is noteworthy that utilization of a carboxylic acid activation/decarboxylation strategy represents an efficient approach for the domino Michael/annulation reaction of the chemically inert coumarin moiety. This protocol could expand candidate libraries, that will benefit the requirement for new bioactive molecules.
Key words
dihydrocoumarins - pyrrolidines - spirooxindoles - 3-isothiocyanato oxindoles - catalyst-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610875.
- Supporting Information
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For selected examples, see:
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For representative examples, see: