Fekete, B., Palkó, M., Haukka, M., & Fülöp, F. (2017). Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol. Molecules, 22 (4), 613. doi:10.3390/molecules22040613
From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the
preparation of pyrrolo[1,2-a]pyrimidine enantiomers is reported. The synthesis is based on domino
ring-closure followed by microwave-induced retro Diels-Alder (RDA) protocols, where the chirality
of the desired products is transferred from norbornene derivatives. The stereochemistry of the
synthesized compounds was proven by X-ray crystallography. The absolute configuration of the
product is determined by the configuration of the starting amino hydroxamic acid.