Construction of Bridged and Fused Bicyclic Skeletons via Intramolecular Addition of Nucleophiles to (η4-Diene)Fe(CO)3 Complexes Bearing Functionalized Side Chains

Ming Chang P. Yeh; B. A. Sheu; H. W. Fu; S. I. Tau; L. W. Chuang

doi:10.1021/ja00067a007

Construction of Bridged and Fused Bicyclic Skeletons via Intramolecular Addition of Nucleophiles to (η⁴-Diene)Fe(CO)₃ Complexes Bearing Functionalized Side Chains

Ming Chang P. Yeh^*, B. A. Sheu, H. W. Fu, S. I. Tau, L. W. Chuang

^*Corresponding author for this work

Department of Chemistry

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

77 Citations (Scopus)

Abstract

Reaction of lithium diisopropylamide (LDA) with (η⁴-1,3-cyclohexadiene)Fe(CO)₃ complexes bearing functionalized side chains at C-5, under an atmosphere of carbon monoxide, gives bridged bicyclo[3.2.1]octene and bicyclo[3.3.1]nonene systems after electrophilic quenching, whereas larger rings cannot be obtained in this series. Under the same reaction conditions, intramolecular cyclization of acyclic (η⁴-1,3-butadiene)Fe(CO)₃ complexes with functionalized side chains at the terminal position of the diene ligands furnishes fused bicyclo[3.3.0]octanone and bicyclo[4.3.0]nonanone derivatives after acid quenching. The iron-mediated intramolecular nucleophilic addition allows for the direct stereocontrol of four stereogenic centers of these fused bicyclic skeletons.

Original language	English
Pages (from-to)	5941-5952
Number of pages	12
Journal	Journal of the American Chemical Society
Volume	115
Issue number	14
DOIs	https://doi.org/10.1021/ja00067a007
Publication status	Published - 1993 Jul 1

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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Construction of Bridged and Fused Bicyclic Skeletons via Intramolecular Addition of Nucleophiles to (η⁴-Diene)Fe(CO)₃ Complexes Bearing Functionalized Side Chains. / Yeh, Ming Chang P.; Sheu, B. A.; Fu, H. W. et al.
In: Journal of the American Chemical Society, Vol. 115, No. 14, 01.07.1993, p. 5941-5952.

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

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abstract = "Reaction of lithium diisopropylamide (LDA) with (η4-1,3-cyclohexadiene)Fe(CO)3 complexes bearing functionalized side chains at C-5, under an atmosphere of carbon monoxide, gives bridged bicyclo[3.2.1]octene and bicyclo[3.3.1]nonene systems after electrophilic quenching, whereas larger rings cannot be obtained in this series. Under the same reaction conditions, intramolecular cyclization of acyclic (η4-1,3-butadiene)Fe(CO)3 complexes with functionalized side chains at the terminal position of the diene ligands furnishes fused bicyclo[3.3.0]octanone and bicyclo[4.3.0]nonanone derivatives after acid quenching. The iron-mediated intramolecular nucleophilic addition allows for the direct stereocontrol of four stereogenic centers of these fused bicyclic skeletons.",

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AU - Yeh, Ming Chang P.

AU - Sheu, B. A.

AU - Fu, H. W.

AU - Tau, S. I.

AU - Chuang, L. W.

PY - 1993/7/1

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N2 - Reaction of lithium diisopropylamide (LDA) with (η4-1,3-cyclohexadiene)Fe(CO)3 complexes bearing functionalized side chains at C-5, under an atmosphere of carbon monoxide, gives bridged bicyclo[3.2.1]octene and bicyclo[3.3.1]nonene systems after electrophilic quenching, whereas larger rings cannot be obtained in this series. Under the same reaction conditions, intramolecular cyclization of acyclic (η4-1,3-butadiene)Fe(CO)3 complexes with functionalized side chains at the terminal position of the diene ligands furnishes fused bicyclo[3.3.0]octanone and bicyclo[4.3.0]nonanone derivatives after acid quenching. The iron-mediated intramolecular nucleophilic addition allows for the direct stereocontrol of four stereogenic centers of these fused bicyclic skeletons.

AB - Reaction of lithium diisopropylamide (LDA) with (η4-1,3-cyclohexadiene)Fe(CO)3 complexes bearing functionalized side chains at C-5, under an atmosphere of carbon monoxide, gives bridged bicyclo[3.2.1]octene and bicyclo[3.3.1]nonene systems after electrophilic quenching, whereas larger rings cannot be obtained in this series. Under the same reaction conditions, intramolecular cyclization of acyclic (η4-1,3-butadiene)Fe(CO)3 complexes with functionalized side chains at the terminal position of the diene ligands furnishes fused bicyclo[3.3.0]octanone and bicyclo[4.3.0]nonanone derivatives after acid quenching. The iron-mediated intramolecular nucleophilic addition allows for the direct stereocontrol of four stereogenic centers of these fused bicyclic skeletons.

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Construction of Bridged and Fused Bicyclic Skeletons via Intramolecular Addition of Nucleophiles to (η⁴-Diene)Fe(CO)₃ Complexes Bearing Functionalized Side Chains

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