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

J Ichikawa; M Fujiwara; S Miyazaki; M Ikemoto; T Okauchi; T Minami

doi:10.1021/ol0161458

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

Org Lett. 2001 Jul 26;3(15):2345-8. doi: 10.1021/ol0161458.

Authors

J Ichikawa¹, M Fujiwara, S Miyazaki, M Ikemoto, T Okauchi, T Minami

Affiliation

¹ Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. [email protected]

PMID: 11463312
DOI: 10.1021/ol0161458

Abstract

[reaction: see text] 3-Fluoro-5-methylene-2-cyclopentenone is treated with appropriate nucleophiles and Lewis acids to undergo regioselective 1,2-addition, exocyclic 1,4-addition, and endocyclic 1,4-addition, leading to 3-substituted 4-methylene-2-cyclopentenones, 5-substituted 3-fluoro-2-cyclopentenones, and 3-substituted 5-methylene-2-cyclopentenones in good yields, respectively.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclopentanes / chemical synthesis*
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry
Stereoisomerism

Substances

Cyclopentanes
Hydrocarbons, Fluorinated
cyclopentenone