Stereoselective Syntheses of Chiral (3S,9bS)-1,2,3,9b-Tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones.

Abstract Chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones 11a–11f, 14b,14c and 17a,b were prepared in 78–93% yields with high stereoselectivities (d.e. >99%) by the intermolecular condensations of 2-formylbenzoic acids 10 or 13 or 2-acetylbenzoic acid 15 with chiral diamines 9a–9f and 9h. Compounds 9a–9f and 9h were readily prepared in three steps from optically active N-Boc-α-amino acids 5a–5d.