Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated Dihydroheteroles

Takeshi Fujita; Masahiro Ikeda; Masahiro Hattori; Kotaro Sakoda; Junji Ichikawa

doi:10.1055/s-0033-1340857

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(11): 1493-1505
DOI: 10.1055/s-0033-1340857

paper

Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated Dihydroheteroles

Autor*innen

Takeshi Fujita

^aDivision of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan Fax: +81(29)8534237 eMail: junji@chem.tsukuba.ac.jp
Masahiro Ikeda

^aDivision of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan Fax: +81(29)8534237 eMail: junji@chem.tsukuba.ac.jp
Masahiro Hattori

^aDivision of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan Fax: +81(29)8534237 eMail: junji@chem.tsukuba.ac.jp
Kotaro Sakoda

^bDepartment of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Junji Ichikawa*

^aDivision of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan Fax: +81(29)8534237 eMail: junji@chem.tsukuba.ac.jp

Abstract

Alle Artikel dieser Rubrik

Abstract

Metal enolates and enamides bearing difluoroallylic moieties underwent nucleophilic 5-endo-trig cyclization, a process considered to be disfavored according to Baldwin’s rules. Whereas no C-cyclization was observed in these reactions, O- and N-cyclization proceeded exclusively to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans and -2,3-dihydropyrroles, respectively.

Key words

cyclizations - fluorine - heterocycles - furans - pyrroles - ring closure

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Referenzen

References

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