Issue 3, 2023

Catalytic photochemical enantioselective α-alkylation with pyridinium salts

Abstract

We have developed a chiral amine catalyzed enantioselective α-alkylation of aldehydes with amino acid derived pyridinium salts as alkylating reagents. The reaction proceeds in the presence of visible light and in the absence of a photocatalyst via a light activated charge-transfer complex. We apply this photochemical stereoconvergent process to the total synthesis of the lignan natural products (−)-enterolactone and (−)-enterodiol. Mechanistic studies support the ground-state complexation of the reactive components followed by divergent charge-transfer processes involving catalyst-controlled radical chain and in-cage radical combination steps.

Graphical abstract: Catalytic photochemical enantioselective α-alkylation with pyridinium salts

Supplementary files

Article information

Article type
Edge Article
Submitted
11 Oct 2022
Accepted
28 Nov 2022
First published
08 Dec 2022
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, 586-592

Catalytic photochemical enantioselective α-alkylation with pyridinium salts

S. R. Yetra, N. Schmitt and U. K. Tambar, Chem. Sci., 2023, 14, 586 DOI: 10.1039/D2SC05654B

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