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 language | English (US) |
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Pages (from-to) | 586-592 |
Number of pages | 7 |
Journal | Chemical Science |
Volume | 14 |
Issue number | 3 |
DOIs | |
State | Published - Dec 8 2022 |
ASJC Scopus subject areas
- General Chemistry