Issue 23, 2023

Asymmetric imino-acylation of alkenes enabled by HAT-photo/nickel cocatalysis

Abstract

By merging nickel-mediated facially selective aza-Heck cyclization and radical acyl C–H activation promoted by tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst, we accomplish an asymmetric imino-acylation of oxime ester-tethered alkenes with readily available aldehydes as the acyl source, enabling the synthesis of highly enantioenriched pyrrolines bearing an acyl-substituted stereogenic center under mild conditions. Preliminary mechanistic studies support a Ni(I)/Ni(II)/Ni(III) catalytic sequence involving the intramolecular migratory insertion of a tethered olefinic unit into the Ni(III)–N bond as the enantiodiscriminating step.

Graphical abstract: Asymmetric imino-acylation of alkenes enabled by HAT-photo/nickel cocatalysis

Supplementary files

Article information

Article type
Edge Article
Submitted
14 Apr 2023
Accepted
19 May 2023
First published
22 May 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, 6449-6456

Asymmetric imino-acylation of alkenes enabled by HAT-photo/nickel cocatalysis

R. Wang and C. Wang, Chem. Sci., 2023, 14, 6449 DOI: 10.1039/D3SC01945D

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