Catalytic photochemical enantioselective α-alkylation with pyridinium salts

Santhivardhana Reddy Yetra, Nathan Schmitt, Uttam K. Tambar

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)586-592
Number of pages7
JournalChemical Science
Volume14
Issue number3
DOIs
StatePublished - Dec 8 2022
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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