✦ LIBER ✦
ChemInform Abstract: Selective One-Step Synthesis of Enantiopure cis-2,5-Disubstituted Pyrrolidines or cis-3,6-Disubstituted Piperidines from the (2R,2′R)-(1,2-Ethanediyl)bis-aziridine.
✍ Scribed by S. FORT; I. MCCORT; A. DUREAULT; J.-C. DEPEZAY
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 33 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Selective One-Step Synthesis of Enantiopure cis-2,5-Disubstituted Pyrrolidines or cis-3,6-Disubstituted Piperidines from the (2R,2'R)-(1,2-Ethanediyl)bis-aziridine.
-Chromatographic purification of the optically active bis-aziridine (I) results in a 5-exo-tet aminocyclization to the cis-2,5-disubstituted pyrrolidine (II). A similar reaction takes place with the nucleophiles (III) and (VI) in aprotic media whereas hydroxylated reagents in protic media yield 3-oxy substituted piperidines (IX) via a 6-exo-tet cyclization.