Intramolecular Addition of Nucleophiles to (η4-Diene)Fe(CO)3 Complexes Bearing Functionalized Side Chains at C-2

Jeng Long Wang; Chuen Her Ueng; Su Jun Cheng; Ming Chang P. Yeh

doi:10.1021/om00023a055

Intramolecular Addition of Nucleophiles to (η⁴-Diene)Fe(CO)₃ Complexes Bearing Functionalized Side Chains at C-2

Jeng Long Wang, Chuen Her Ueng, Su Jun Cheng, Ming Chang P. Yeh^*

^*Corresponding author for this work

Department of Chemistry

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

9 Citations (Scopus)

Abstract

The addition of a variety of highly functionalized zinc-copper reagents RCu(CN)ZnI to (η⁴-2-formylbuta-1,3-diene)Fe(CO)₃ complex in the presence of an excess of boron trifluoride etherate proceeds in a highly diastereoselective fashion to afford dienol complexes in good yields. Intramolecular cyclization of a cyano-substituted dienol complex containing a threecarbon side chain using lithium diisopropylamide (LDA) produces (σ,η³-allyl)tricarbonyliron complexes, whereas treatments of the cyano-substituted dienol complex containing a fourcarbon side chain with LDA furnishes fused tetracarbonylbicyclo[4.3.0]ferranonanones at -78 °C and complexes of the trimethylenemethane type at 25 °C.

Original language	English
Pages (from-to)	4453-4461
Number of pages	9
Journal	Organometallics
Volume	13
Issue number	11
DOIs	https://doi.org/10.1021/om00023a055
Publication status	Published - 1994 Nov 1

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "The addition of a variety of highly functionalized zinc-copper reagents RCu(CN)ZnI to (η4-2-formylbuta-1,3-diene)Fe(CO)3 complex in the presence of an excess of boron trifluoride etherate proceeds in a highly diastereoselective fashion to afford dienol complexes in good yields. Intramolecular cyclization of a cyano-substituted dienol complex containing a threecarbon side chain using lithium diisopropylamide (LDA) produces (σ,η3-allyl)tricarbonyliron complexes, whereas treatments of the cyano-substituted dienol complex containing a fourcarbon side chain with LDA furnishes fused tetracarbonylbicyclo[4.3.0]ferranonanones at -78 °C and complexes of the trimethylenemethane type at 25 °C.",

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AU - Cheng, Su Jun

AU - Yeh, Ming Chang P.

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N2 - The addition of a variety of highly functionalized zinc-copper reagents RCu(CN)ZnI to (η4-2-formylbuta-1,3-diene)Fe(CO)3 complex in the presence of an excess of boron trifluoride etherate proceeds in a highly diastereoselective fashion to afford dienol complexes in good yields. Intramolecular cyclization of a cyano-substituted dienol complex containing a threecarbon side chain using lithium diisopropylamide (LDA) produces (σ,η3-allyl)tricarbonyliron complexes, whereas treatments of the cyano-substituted dienol complex containing a fourcarbon side chain with LDA furnishes fused tetracarbonylbicyclo[4.3.0]ferranonanones at -78 °C and complexes of the trimethylenemethane type at 25 °C.

AB - The addition of a variety of highly functionalized zinc-copper reagents RCu(CN)ZnI to (η4-2-formylbuta-1,3-diene)Fe(CO)3 complex in the presence of an excess of boron trifluoride etherate proceeds in a highly diastereoselective fashion to afford dienol complexes in good yields. Intramolecular cyclization of a cyano-substituted dienol complex containing a threecarbon side chain using lithium diisopropylamide (LDA) produces (σ,η3-allyl)tricarbonyliron complexes, whereas treatments of the cyano-substituted dienol complex containing a fourcarbon side chain with LDA furnishes fused tetracarbonylbicyclo[4.3.0]ferranonanones at -78 °C and complexes of the trimethylenemethane type at 25 °C.

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Intramolecular Addition of Nucleophiles to (η⁴-Diene)Fe(CO)₃ Complexes Bearing Functionalized Side Chains at C-2

Abstract

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