A Enamide-based diastereoselective synthesis of isoindolo[2,1-a]quinolin-11(5H)-ones with three contiguous stereogenic centers

07 November 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A stereoselective synthesis of isoindolo[2,1-a]quinolin-11(5H)-ones containing three contiguous stereogenic centers is described. This Lewis-acid mediated reaction of enamides with N-aryl- affords the desired fused heterocyclic isoindolinones in high yields and diastereoselectivities. Scope and limitations of this method are discussed. The stereochemical outcome of this transformation indicates a stepwise reaction pathway.

Keywords

enamide
acyliminium ion
Povarov reaction
nitrogen heterocycle
diastereoselectivity

Supplementary materials

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Description
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Supporting Information
Description
Experimental procedures, analytical data and copies of NMR spectra
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X-Ray data
Description
cif and checkcif files for compounds syn-11a, anti-11a, anti-11b, syn-11d, syn-11g, syn-11i and 12b (CCDC 2189964-2189970)
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