Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic β-keto esters with terminal alkynes

Yoichiro Kuninobu, Junya Morita, Mitsumi Nishi, Atsushi Kawata, Kazuhiko Takai

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Treatment of cyclic βKeto esters with terminal alkynes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)3(thf)] 2, gave bicyclo[3.3.1]nonene derivatives. The reaction conditions and yields of the bicyclo[3.3.1]nonenes were improved by the sequential use of tetrabutylammonium fluoride (TBAF) after the rhenium-catalyzed reactions.

Original languageEnglish
Pages (from-to)2535-2537
Number of pages3
JournalOrganic Letters
Volume11
Issue number12
DOIs
Publication statusPublished - Jun 18 2009
Externally publishedYes

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Rhenium
Alkynes
rhenium
alkynes
esters
Esters
Carbon Monoxide
fluorides
Derivatives
tetrabutylammonium

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic β-keto esters with terminal alkynes. / Kuninobu, Yoichiro; Morita, Junya; Nishi, Mitsumi; Kawata, Atsushi; Takai, Kazuhiko.

In: Organic Letters, Vol. 11, No. 12, 18.06.2009, p. 2535-2537.

Research output: Contribution to journalArticle

Kuninobu, Yoichiro ; Morita, Junya ; Nishi, Mitsumi ; Kawata, Atsushi ; Takai, Kazuhiko. / Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic β-keto esters with terminal alkynes. In: Organic Letters. 2009 ; Vol. 11, No. 12. pp. 2535-2537.
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