Issue 11, 2023

Catalytic enantioselective alkenylation–heteroarylation of olefins: stereoselective syntheses of 5–7 membered azacycles and oxacycles

Abstract

Catalytic enantioselective domino alkenylation–heteroarylation of nonconjugated iododienes proceeded with excellent stereoselectivity and broad scope of substrates. The reaction enables stereoselective syntheses of substituted azacycles such as piperidine, pyrrolidine azepine and dihydropyrans carrying new quaternary stereocenters. Mechanistically, C–H bonds of heterocycles were activated by lithium alkoxides via reversible deprotonation, rather than conventional palladium(II)-assisted metalation processes. Many types of heteroarenes can be used, including not only azoles (such as thiazoles, oxazoles, imidazoles and oxadiazoles), but also nonazoles (thiophene, furan and azine N-oxides).

Graphical abstract: Catalytic enantioselective alkenylation–heteroarylation of olefins: stereoselective syntheses of 5–7 membered azacycles and oxacycles

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Dec 2022
Accepted
16 Feb 2023
First published
17 Feb 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 3010-3017

Catalytic enantioselective alkenylation–heteroarylation of olefins: stereoselective syntheses of 5–7 membered azacycles and oxacycles

Z. Ma, L. Sun and J. S. Zhou, Chem. Sci., 2023, 14, 3010 DOI: 10.1039/D2SC07117G

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