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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 Jäger

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 493 KB
Volume: 2001
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200104)2001:7<1293::aid-ejoc1293>3.0.co;2-4

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✦ Synopsis

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 employing organolithium compounds or Lewis acids

Synthesis of Glycosidase-Inhibiting Iminopolyols by CopeϪ House Cyclization of Unsaturated Hydroxylamines, III. Ϫ Part II: Ref. [1] [ ‡][ ‡] Ref. [2] [a]

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ChemInform Abstract: Synthesis of Glycos

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.

✍ Andreas M. Palmer; Volker Jaeger 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 38 KB 👁 1 views