Abstract
Diastereomers of tetracyclic pyrrolopyrimidine derivatives 2 and 3 were prepared in a three-step domino reaction from DIEXO-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide with levulinic acid or P-toluoylpropionic acid. When subjected to a microwave-mediated retro-Diels-Alder reaction, these tetracycles furnished bicyclic pyrrolo[1,2- A]pyrimidines through the loss of cyclopentadiene. When enantiomeric DIEXO-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide was used, the products were enantiomeric heterocycles with ee >99%, demonstrating that the title compound is an excellent chiral source.
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