Synthesis of 4-(Arylmethyl)proline Derivatives

Synthesis of 4-(Arylmethyl)proline Derivatives: S. Loosli, C. Foletti, M. Papmeyer, H. Wennemers
Synlett 2019, 30, 508–510

The peculiarity and unique properties of proline – the only proteinogenic amino acid with a cyclic backbone – have prompted chemists to design, synthesize and study the properties of countless proline derivatives and analogues. Proline derivatives carrying arylmethyl functions at the γ-carbon (Cγ), however, have not been extensively studied, possibly owing to the lack of effective synthetic strategies. The group of Professor Helma Wennemers from ETH Zurich (Switzerland) recently published a synthesis of 4-(arylmethyl)prolines which relies on Suzuki cross-couplings and permits access to a variety of 4-substituted proline derivatives bearing various aryl moieties.

Professor Wennemers said: “Proline derivatives bearing different substituents at Cγ are important tools to interrogate the chemistry and biology or processes ranging from ion-gating and the structural integrity of skin to asymmetric catalysis.”
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