CC BY-NC-ND 4.0 · Synlett 2023; 34(20): 2374-2378
DOI: 10.1055/a-2061-0855
account
Special Issue Dedicated to Prof. Hisashi Yamamoto

Synthesis of Functionalized Spirooxindole Polycycles: Use of Cyclic 1,3-Diones as Reactants or as Condition-Tuning Molecules

Muhammad Sohail
,
Fujie Tanaka
This study was supported by the Okinawa Institute of Science and Technology Graduate University.


Abstract

This account describes the strategies for the synthesis of functionalized spirooxindole polycycles, including enantiomerically enriched forms, that we have developed and reported. The syntheses of these complex molecules were accomplished in a few steps starting from relatively simple oxindole derivatives and other reactants. Organocatalytic reactions involved in kinetic resolution or in dynamic kinetic transformation led to the formation of products with high diastereo- and/or enantioselectivities. Cyclic 1,3-diones, such as 1,3-cyclohexanedione, were used as reactants to provide two reaction sites for the construction of polycyclic ring systems. To tune the reaction conditions, 2-methyl-1,3-cyclohexanedione was employed. The developed methods enabled the synthesis of complex functionalized spirooxindole polycycles bearing up to seven stereogenic centers, and will be useful for the synthesis of potentially bioactive molecules.

1 Introduction

2 Formal (4+1) Cycloaddition and Enantioselective Michael/Henry Cascade Reactions

3 Dynamic Stereoselective Aldol/Oxacyclization Cascade Reactions

4 Dynamic Kinetic Asymmetric Transformation: Diastereo- and Enantioconvergent Michael/Henry Reactions

5 Dimerization Reactions

6 Conclusion



Publication History

Received: 20 February 2023

Accepted after revision: 22 March 2023

Accepted Manuscript online:
23 March 2023

Article published online:
26 April 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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