Regioselective nucleophilic additions to cross-conjugated dienone system bearing beta-fluorine: A versatile approach to highly substituted 2-cyclopentenones

Authors
Ichikawa, J Fujiwara, M Miyazaki, S Ikemoto, M Okauchi, T Minami, T
Citation
J. Ichikawa et al., Regioselective nucleophilic additions to cross-conjugated dienone system bearing beta-fluorine: A versatile approach to highly substituted 2-cyclopentenones, ORG LETT, 3(15), 2001, pp. 2345-2348
Citations number
35
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
15
Year of publication
2001
Pages
2345 - 2348
Database
ISI
SICI code
1523-7060(20010726)3:15<2345:RNATCD>2.0.ZU;2-G
Abstract
[GRAPHICS] 3-Fluoro-5-methylene-2-cyclopentenone is treated with appropriate nucleophi les and Lewis acids to undergo regioselective 1,2-addition, exocyclic 1,4-a ddition, and endocyclic 1,4 addition, leading to 3-substituted 4-methylene- 2-cyclopentenones, 5-substituted 3-fluoro-2-cyclopentenones, and 3-substitu ted 5-methylene-2-cyclopentenones in good yields, respectively.