ChemInform Abstract: Diastereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidine N-Oxides by the Retro-Cope Elimination.
β Scribed by Mark C. Bagley; Julie Tovey
- Publisher
- John Wiley and Sons
- Year
- 2001
- Weight
- 28 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0931-7597
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π SIMILAR VOLUMES
I) and addition of nitrones (II) results in a smooth condensation to give the unsaturated hydroxylamines (III) stereoselectively. These undergo reverse-Cope cyclizations at room temperature leading to the diastereomeric mixture of pyrrolidine-N-oxides (IV) and (V). -
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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-disubst