Synthesis and structure of a heterocyclic ansa pyrrole amino acid

Georg Dirscherl (1) , Parham Rooshenas (2) , Peter R. Schreiner (2) , Frédéric Lamaty (3) , Burkhard König (1)

1 Institut für Organische Chemie
2 JLU - Justus-Liebig-Universität Gießen = Justus Liebig University
3 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

We report a synthetic route to ansa pyrrole amino acids via olefin ring-closing metathesis of diene precursors in the presence of Grubbs I catalyst. The dienes were prepared by Grignard addition to pyrrole sulfinyl imines. The success of the macrocyclic ring closure depends on the dienes structure and only in the case of the 13-membered compound 28 sufficient material could be isolated by preparative HPLC separation to investigate its structure spectroscopically. As also rationalized by our computations at the B3LYP/6-311+G(d.p)//B3LYP/6-31G(d) level of theory 28 is configurationally stable.

Mots clés: Pyrrole; sulfinyl amine; diastereoselectivity; RCM; Ring Closing Metathesis

Domaines: Chimie organique

Georg Dirscherl, Parham Rooshenas, Peter R. Schreiner, Frédéric Lamaty, Burkhard König. Synthesis and structure of a heterocyclic ansa pyrrole amino acid. Tetrahedron, 2008, 64 (13), pp.3005-3016. ⟨10.1016/j.tet.2008.01.061⟩. ⟨hal-00258762⟩