A Click‐Type Reaction of ( RRR )‐α‐Tocopherol and Related 6‐Chromanols Allowing a One Pot Derivatisation of All Fat‐Soluble Vitamins
Year: 2025
Type: article
Abstract: ABSTRACT ( RRR )‐α‐tocopherol reacts with 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (PTAD) at ambient conditions in a fast formal [6+2+2] addition reaction yielding four pairs of diastereomers, three of them containing novel heterocyclic ring systems. Structure elucidation required customized 3,5‐ 13 C 2 ,4‐ 15 N labelled PTAD to establish the connectivity of the PTAD units using 4–5 J 1 H‐ 13 C, 2 J 13 C‐ 13 C, and 1 J 13 C‐ 14 N NMR correlations. Absolute stereochemistry was determined based on calculated CD spectra compared to experimental data. The reaction occurred also with related 6‐chromanols and required a free phenolic hydroxy group. As one possibility, the addition of the first PTAD involves a hetero‐Alder‐ene reaction, followed by a Diels–Alder or alternative addition / cyclization of a second PTAD. Together with the derivatization of vitamin K and the known reactions with vitamins A and D, PTAD can thus derivatize all fat‐soluble vitamins in a one pot reaction, offering potential new applications for their analysis in complex matrices.
Source: Chemistry - A European Journal
Institution: DSM-Firmenich AG (Switzerland)
Language: English
Subfield: Spectroscopy
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4416824544