Sequential additions of nucleophiles to tricarbonyl(η4-cycloheptadienyl)iron tetrafluoroborate

Wulf Blankenfeldt, Jin Wei Liao, Li Chin Lo, Ming Chang P. Yeh

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Reaction of lithium diisopropylamide (LDA) with (η4-cycloheptadiene)Fe(CO)3 complexes bearing functionalized side chains at C-5, under an atmosphere of carbon monoxide, gives the bridged bicyclo[4.2.1.]nonane derivative 3 after acid quenching, whereas treatments of the reaction mixture with carbon electrophiles furnished the tricyclo[5.2.1.04,8]decane derivative 7. The iron-mediated intramolecular nucleophilic addition allows for the direct stereocontrol of six stereogenic centers of the tricyclic skeleton.

Original languageEnglish
Pages (from-to)7361-7364
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number41
DOIs
Publication statusPublished - 1996 Oct 7

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Nucleophiles
Carbon Monoxide
Atmosphere
Skeleton
Bearings (structural)
Carbon
Iron
Derivatives
Acids
Quenching
diisopropylamine
nonane
decane

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Sequential additions of nucleophiles to tricarbonyl(η4-cycloheptadienyl)iron tetrafluoroborate. / Blankenfeldt, Wulf; Liao, Jin Wei; Lo, Li Chin; Yeh, Ming Chang P.

In: Tetrahedron Letters, Vol. 37, No. 41, 07.10.1996, p. 7361-7364.

Research output: Contribution to journalArticle

Blankenfeldt, Wulf ; Liao, Jin Wei ; Lo, Li Chin ; Yeh, Ming Chang P. / Sequential additions of nucleophiles to tricarbonyl(η4-cycloheptadienyl)iron tetrafluoroborate. In: Tetrahedron Letters. 1996 ; Vol. 37, No. 41. pp. 7361-7364.
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