A Novel Cyclopentene Annulation Method Based on Conjugate Addition Reactions of α-Cyano Carbanion Species

A Novel Cyclopentene Annulation Method Based on Conjugate Addition Reactions of α-Cyano Carbanion Species

A new cyclopentene annulation method based on a conjugate addition reaction with 4‐methoxybut‐3‐enenitrile was developed. Treatment of a cyclic enone with the potassium carbanion of the nitrile followed by acetic anhydride afforded an enol acetate, which underwent an HCl‐mediated intramolecular cycl...

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Bibliographic Details
Published in:European Journal of Organic Chemistry Vol. 2006; no. 2; pp. 328 - 334
Main Authors: Tanino, Keiji, Tomata, Yoshihide, Shiina, Yasuhiro, Miyashita, Masaaki
Format: Book Review Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 01-01-2006
WILEY‐VCH Verlag
Subjects:
Annulation
Cyanides
Cyclization
Enones
Michael addition
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Summary:A new cyclopentene annulation method based on a conjugate addition reaction with 4‐methoxybut‐3‐enenitrile was developed. Treatment of a cyclic enone with the potassium carbanion of the nitrile followed by acetic anhydride afforded an enol acetate, which underwent an HCl‐mediated intramolecular cyclization reaction to yield a bicyclo[n.3.0]alkenone derivative in good yield. A lipase‐mediated optical resolution of the annulation product provided a new chiral building block for steroids and other natural compounds.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Bibliography:istex:EBBA6EBE44C725C85979877F75CDC85C0B2635C0
ark:/67375/WNG-4SFWK6S3-2
ArticleID:EJOC200500759
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500759