Abstract
Abstract The first enantioselective synthesis of a photoreactive (R)-β-phenylalanine is described. In the key step, m-diazirinyl-substituted benzaldehyde is converted to a chiral sulfinimine in a Ti(OEt)4- mediated reaction, followed by diastereoselective enolate addition. The absolute configuration of photo (R)-β-phenylalanine was confirmed by Mosher analysis. The photo amino acid proved to be thermally stable under standard laboratory conditions. Irradiation in toluene afforded cycloheptatriene=norcaradiene valence tautomers, together with carbene benzylation. Quantumchemical calculations indicate a small triplet-singlet gap.
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