One-Pot Diastereoselective Synthesis of Pyrrolopiperazine-2,6-diones by a Ugi/Nucleophilic Substitution/N-Acylation Sequence

The diastereoselective synthesis of two families of pyrrolopiperazine-2,6-diones is presented. These compounds were prepared by one-pot Ugi/nucleophilic substitution/N-acylation/debenzoylation/(elimination) sequences. This novel route provides straightforward access to a wide variety of pyrrolopiperazine-2,6-diones with high chemical yields and complete diastereoselectivities. The proposed synthetic strategy poses a significant improvement compared to the syntheses of pyrrolopiperazine-2,6-diones previously described, as it allows introduction of different substituents to the C4 position and the diastereoselective generation of new stereogenic center on the bridgehead carbon (C8a).

Automated summary

The diastereoselective synthesis of two families of pyrrolopiperazine-2,6-diones is achieved through a novel one-pot reaction sequence. This method allows for the introduction of various substituents at the C4 position and the generation of a new stereogenic center on the bridgehead carbon (C8a) with high chemical yields and complete diastereoselectivities.