O-(2-Oxopyrrolidin-5-yl)trichloroacetimidates as Amidoalkylating Agents − Synthesis of (+)-Lentiginosine

O-(2-Oxopyrrolidin-5-yl)trichloroacetimidates as Amidoalkylating Agents − Synthesis of (+)-Lentiginosine

N‐α‐Hydroxyalkylamides 6a,b, readily available from L‐tartrate, with trichloroacetonitrile furnish O‐(2‐oxopyrrolidin‐5‐yl)trichloroacetimidates 3a,b. α‐Amido‐alkylation studies of 3a,b with allyl‐trimethylsilane and electron‐rich benzene derivatives as C‐nucleophiles afforded 5‐allyl‐ and 5‐aryl‐2‐...

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Bibliographic Details
Published in:European journal of organic chemistry Vol. 2002; no. 24; pp. 4137 - 4142
Main Authors: El-Nezhawy, Ahmed O. H., El-Diwani, Hoda I., Schmidt, Richard R.
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 01-12-2002
WILEY‐VCH Verlag
Subjects:
Amidoalkylation
Glycosidase Inhibitor
Indolizidines
Lentiginosine
Synthesis
Trichloroacetimidate
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Summary:N‐α‐Hydroxyalkylamides 6a,b, readily available from L‐tartrate, with trichloroacetonitrile furnish O‐(2‐oxopyrrolidin‐5‐yl)trichloroacetimidates 3a,b. α‐Amido‐alkylation studies of 3a,b with allyl‐trimethylsilane and electron‐rich benzene derivatives as C‐nucleophiles afforded 5‐allyl‐ and 5‐aryl‐2‐pyrrolidinones 2a,b, 7a,b, and 8−10. The target compound (+)‐1 and its epimer 15 were readily obtained from 1,5‐diallyl‐2‐pyrrolidinones 2b and 7b, respectively, via ring‐closing metathesis, amide group reduction, and CC‐double bond hydrogenation. (© Wiley‐VCH Verlag GmbH & Co KGaA, 69451 Weinheim, Germany, 2002)
Bibliography:istex:A0965262F1DD37432CC9E6DCA4E0808DB413EDEE
ark:/67375/WNG-Z7VTDSPF-X
ArticleID:EJOC4137
ISSN:1434-193X
1099-0690
DOI:10.1002/1099-0690(200212)2002:24<4137::AID-EJOC4137>3.0.CO;2-X