Traceless chirality transfer from a norbornene β-amino acid to pyrimido[2,1-a]isoindole enantiomers

The synthesis of two enantiomeric pairs of pyrimidoisoindoles 9a, 9b and 10a, 10b is reported. During a domino ring-closure reaction, followed by cycloreversion, the chirality of diendo-(-)-(1R,2S,3MS)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide [(-)-1] was successfully transfered to heterocycles (+)-9a, (+)-10a, (-)-9b, (-)-10b and (-)-10c. (C) 2017 Elsevier Ltd. All rights reserved.