Short Communication

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

  1. Keiji Tanino,
  2. Yoshihide Tomata,
  3. Yasuhiro Shiina,
  4. Masaaki Miyashita

Article first published online: 21 NOV 2005

DOI: 10.1002/ejoc.200500759

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2006, Issue 2, pages 328–334, January 2006

Additional Information

How to Cite

Tanino, K., Tomata, Y., Shiina, Y. and Miyashita, M. (2006), A Novel Cyclopentene Annulation Method Based on Conjugate Addition Reactions of α-Cyano Carbanion Species. Eur. J. Org. Chem., 2006: 328–334. doi: 10.1002/ejoc.200500759

Author Information

  1. Division of Chemistry, Graduate School of Science, Hokkaido University, 060-0810 Sapporo, Japan, Fax: +81-11-706-4920

Publication History

  1. Issue published online: 2 JAN 2006
  2. Article first published online: 21 NOV 2005
  3. Manuscript Received: 4 OCT 2005

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article (HTML) Get PDF (137K)

Keywords:

  • Cyclization;
  • Annulation;
  • Enones;
  • Cyanides;
  • Michael addition

Abstract

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)

View Full Article (HTML) Get PDF (137K)