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

Access to Document

10.1016/0040-4039(96)01656-5

Cite this

@article{df34c04e014243419ed31f8ecaacadc4,

title = "Sequential additions of nucleophiles to tricarbonyl(η4-cycloheptadienyl)iron tetrafluoroborate",

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.",

author = "Wulf Blankenfeldt and Liao, \{Jin Wei\} and Lo, \{Li Chin\} and Yeh, \{Ming Chang P.\}",

year = "1996",

month = oct,

day = "7",

doi = "10.1016/0040-4039(96)01656-5",

language = "English",

volume = "37",

pages = "7361--7364",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "41",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/0030574014

UR - https://www.scopus.com/pages/publications/0030574014#tab=citedBy

U2 - 10.1016/0040-4039(96)01656-5

DO - 10.1016/0040-4039(96)01656-5

M3 - Article

AN - SCOPUS:0030574014

SN - 0040-4039

VL - 37

SP - 7361

EP - 7364

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this