Brønsted-Acid Catalyzed Diastereoselective Synthesis of Spiroisoindolinones from Enamides

18 December 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A highly diastereoselective synthesis of spiroisoindolinones from enamides and 3-hydroxy-isoindolinones is reported. The reaction proceeds rapidly in the presence of para-toluenesulfonic acid as Brønsted acid-catalyst and affords a variety of densely substituted spiroisoindolinoes with three contiguous stereogenic centers in high yields (up to 98%) and diastereoselectivities (up to dr >98:<2:0:0).

Keywords

spirocycles
enamide
stereoselective synthesis
spiroisindolinones

Supplementary materials

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Description
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Supporting Information File 1
Description
Experimental details, spectral data, DOIs for data referring to this study (deposited in the chemotion repository: https://www.chemotion-repository.net/), and copies of NMR spectra for all new compounds
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Supporting Information File 2
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Information on the physical availability of the target com-pounds from the Molecule Archive at KIT (https://compound-platform.eu/home).
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X ray data
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cif and checkcif files for compounds 4a (CCDC 2311285), 4h (CCDC 2311286) and 4p (CCDC 2311287)
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