Organometallic reactions characteristic of chiral heterocyclic compounds: Synthesis and stereo-selective Grignard reaction of chiral 4-oxa-7,7a-diazaperhydroindans

Article abstract of DOI:10.1248/cpb.39.836

New heterocyclic compounds, 6-phenyl-4-oxa-7,7a-diazaperhydroindans (5 and 6), were synthesized by condensation of chiral 2-hydroxyethylhydrazines prepared from (R)-phenylglycinol with γ-chlorobutyraldehyde. The stereoselective Grignard reaction of 5 and 6 proceeded to give chiral 2-substituted 1-[N-(2-hydroxy-1-phenylethyl)amino]pyrrolidines (7a-d and 8a-d). The structures of these products were determined by comparison with authentic samples, and the reaction mechanism is proposed to involve an intermediate iminium salt.