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Published on: September 6, 2019
Stereoselective One-Pot Synthesis of Dihydropyrimido[2,1-a]isoindole-6(2H)-ones
Philipp Kramer1, Julia Schönfeld1, Michael Bolte1
1Department of Biochemistry, Chemistry and Pharmacy, Goethe-University , Max-von-Laue-Strasse 7, 60438 Frankfurt, Germany.
Abstract:
A diastereoselective one-pot synthesis of highly substituted dihydropyrimido[2,1-a]isoindole-6(2H)-ones containing three continuous stereocenters is reported. The reaction sequence is based on a hetero-Diels-Alder reaction between an enimide and a N-acylimine followed by an unprecedented Brønsted acid mediated rearrangement of an intermediate 5,6-dihydro-4H-1,3-oxazine to a pyrimido[2,1-a]isoindole.
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