Issue 5, 2023

Trienamine catalysed unprecedented remote olefin E/Z isomerisation/[4 + 2]-cycloaddition reaction to access spirooxindole hexahydroindoles

Abstract

Herein, for the first time, we report the asymmetric synthesis of an unexpected stereoisomer of spirohexahydroindole via a trienamine-catalysed remote olefin E/Z isomerisation/[4 + 2]-cycloaddition reaction. The reaction afforded a vast library of aesthetically pleasing spirooxindole hexahydroindole scaffolds with exceptional enantio- and diastereo-selectivities (up to 95% yield, 99% ee and >99 : 1 dr). In addition, we demonstrated the synthetic transformation of enantiomerically pure spirooxindole hexahydroindoles to synthesize alkyl homologated spirooxindole hexahydroindole and fluoro-pyranooctahydroindole moieties with four and seven contiguous stereocenters, respectively, in excellent yield and selectivities. We have also demonstrated the evidence for the proposed pathway through NMR investigations.

Graphical abstract: Trienamine catalysed unprecedented remote olefin E/Z isomerisation/[4 + 2]-cycloaddition reaction to access spirooxindole hexahydroindoles

Supplementary files

Article information

Article type
Communication
Submitted
06 Dec 2022
Accepted
23 Dec 2022
First published
06 Jan 2023

Org. Biomol. Chem., 2023,21, 945-949

Trienamine catalysed unprecedented remote olefin E/Z isomerisation/[4 + 2]-cycloaddition reaction to access spirooxindole hexahydroindoles

M. S. Prasad, M. Sivaprakash, S. Bharani and L. R. Chowhan, Org. Biomol. Chem., 2023, 21, 945 DOI: 10.1039/D2OB02228A

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