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ChemInform Abstract: Synthesis of Glycosidase-Inhibiting Iminopolyols by Cope—House Cyclization of Unsaturated Hydroxylamines. Part 3. Pyrrolidine N-Oxides by Stereoselective Addition of Grignard and Lithium Compounds to 4,5-Dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenose N-Benzyl Nitrone and Subsequent Cope—House Cyclization.

✍ Scribed by Andreas M. Palmer; Volker Jaeger

Publisher
John Wiley and Sons
Year
2010
Weight
38 KB
Volume
33
Category
Article
ISSN
0931-7597

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Pyrrolidine N-Oxides by Stereoselective
Pyrrolidine N-Oxides by Stereoselective Addition of Grignard and Lithium Compounds to 4,5-Dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenose N-Benzyl Nitrone and Subsequent Cope−House Cyclization
✍ Andreas M. Palmer; Volker Jäger 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 493 KB

The addition of Grignard reagents to D-erythro-4-pentenose N-benzyl nitrone 5, which is easily accessible from D-ribose, furnishes ω-unsaturated hydroxylamines that readily undergo Cope-House cyclization to afford pyrrolidine N-oxides. The stereoselectivity of the addition step is altered by either