Chemical and Pharmaceutical Bulletin p. 836 - 842 (1991)
Update date:2022-08-03
Topics:
Takahashi
Senda
Higashiyama
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.
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