Issue 63, 2021

Enantioselective synthesis of tetra-substituted tetralines and tetrahydro-indolizines by NHC-catalyzed azolium–enolate cascade

Abstract

NHC-catalyzed cascade reaction of enals with suitably substituted β-(hetero)aryl enones allowing the enantioselective synthesis of tetra-substituted tetralines and tetrahydro indolizines is presented. The catalytically generated chiral α,β-unsaturated acylazoliums from enals under oxidative conditions reacted in a MichaelMichael-lactonization sequence to form the tricyclic δ-lactone products bearing four contiguous stereocentres.

Graphical abstract: Enantioselective synthesis of tetra-substituted tetralines and tetrahydro-indolizines by NHC-catalyzed azolium–enolate cascade

Supplementary files

Article information

Article type
Communication
Submitted
15 Jun 2021
Accepted
07 Jul 2021
First published
09 Jul 2021

Chem. Commun., 2021,57, 7794-7797

Enantioselective synthesis of tetra-substituted tetralines and tetrahydro-indolizines by NHC-catalyzed azolium–enolate cascade

A. Ghosh, S. Barik, S. Shee and A. T. Biju, Chem. Commun., 2021, 57, 7794 DOI: 10.1039/D1CC03165A

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