Issue 53, 2024

Stereoselective synthesis of 6/7/6-fused heterocycles with multiple stereocenters via an internal redox reaction/inverse electron-demand hetero-Diels–Alder reaction sequence

Abstract

A highly stereoselective synthesis of fused heterocycles with multiple stereocenters via an internal redox reaction/inverse electron-demand hetero-Diels–Alder (IEDHDA) reaction sequence is described. The present reaction sequence has three interesting features: (1) complete control of two potentially competitive processes, i.e., hetero-Diels–Alder reaction and [1,5]-hydride shift; (2) one-shot construction of the complicated 6/7/6-fused heterocyclic structure having multiple stereocenters; and (3) high control of its stereoselectivity. When alkenylidene barbiturates with an allyl benzyl ether moiety were treated with a catalytic amount of Sc(OTf)3 and 2,2′-bipyridine, the internal redox reaction/IEDHDA reaction proceeded successively to afford 6/7/6-fused heterocycles in good chemical yields with good to excellent diastereoselectivities.

Graphical abstract: Stereoselective synthesis of 6/7/6-fused heterocycles with multiple stereocenters via an internal redox reaction/inverse electron-demand hetero-Diels–Alder reaction sequence

Supplementary files

Article information

Article type
Communication
Submitted
15 May 2024
Accepted
04 Jun 2024
First published
05 Jun 2024

Chem. Commun., 2024,60, 6797-6800

Stereoselective synthesis of 6/7/6-fused heterocycles with multiple stereocenters via an internal redox reaction/inverse electron-demand hetero-Diels–Alder reaction sequence

D. Sakai, T. Kojima, T. Kawasaki-Takasuka and K. Mori, Chem. Commun., 2024, 60, 6797 DOI: 10.1039/D4CC02351J

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