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

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

doi:10.1016/0040-4039(96)01656-5

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

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

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 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[5.2.1.0^4,8]decane derivative 7. The iron-mediated intramolecular nucleophilic addition allows for the direct stereocontrol of six stereogenic centers of the tricyclic skeleton.

Original language	English
Pages (from-to)	7361-7364
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	41
DOIs	https://doi.org/10.1016/0040-4039(96)01656-5
Publication status	Published - 1996 Oct 7

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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T1 - Sequential additions of nucleophiles to tricarbonyl(η4-cycloheptadienyl)iron tetrafluoroborate

AU - Blankenfeldt, Wulf

AU - Liao, Jin Wei

AU - Lo, Li Chin

AU - Yeh, Ming Chang P.

PY - 1996/10/7

Y1 - 1996/10/7

N2 - 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.

AB - 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.

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

Abstract

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