Preparation of enantioenriched iodinated pyrrolinones by iodocyclization of α-amino-ynones

Rosella Spina (1, 2) , Evelina Colacino (1) , Bartolo Gabriele (2) , Giuseppe Salerno (3) , Jean Martinez (1) , Frédéric Lamaty (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 Dipartimento di Scienze Farmaceutiche and Dipartimento di Chimica
3 Dipartimento di Chimica

The unprecedented electrophilic iodo-mediated cyclization of α-amino-ynones afforded enantiomerically enriched β-iodopyrrolin-4-ones in excellent yields under mild conditions. The starting substituted α-amino-ynones were obtained from the chiral pool by selective mono-addition of an organolithium to optically pure N-protected carboxyanhydrides of amino acids (UNCAs).

Domaines: Chimie organique

Rosella Spina, Evelina Colacino, Bartolo Gabriele, Giuseppe Salerno, Jean Martinez, et al.. Preparation of enantioenriched iodinated pyrrolinones by iodocyclization of α-amino-ynones. Organic & Biomolecular Chemistry, 2012, 10, pp.9085-9089. ⟨10.1039/c2ob26427g⟩. ⟨hal-00748609⟩