Synthesis of 5-Substituted α,β-Butenolides by Iron-promoted Intramolecular Cyclocarbonylation: Addition of Organometallic Reagents to Iron-substituted Enals

Möller, Christian; Mikulás, Mark; Wierschem, Frank; Rück‐Braun, K.

doi:10.1055/s-2000-6497

Cited by 10 publications

(4 citation statements)

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“…Removal of the solvent left a crude mixture, which was separated by column chromatography (hexane/ethyl acetate = 10/1) to give furan‐3(5 H )‐ones. Except for known 4a , 4b , 4g , 4h and 4i , all new products prepared by the above procedure were characterized spectroscopically as shown below.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐catalyzed carbonylative cyclization of 3‐bromoallyl alcohols leading to furan‐2(5H)‐ones

Lee

Cho

2012

Applied Organom Chemis

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Section: Methodsmentioning

confidence: 99%

Palladium‐catalyzed carbonylative cyclization of 3‐bromoallyl alcohols leading to furan‐2(5H)‐ones

Lee

Cho

2012

Applied Organom Chemis

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“…The synthesis of α,β-unsaturated butenolides has been reported by an intramolecular cyclocarbonylation reaction. 30 Reduction of the aldehyde with a nucleophile allows the alkoxide to cyclise onto the iron group to produce the lactone (Scheme 13). The same principle has also been extended to the preparation of lactams through the reaction of amines.…”

Section: Scheme 9 Scheme 10mentioning

confidence: 99%

Applications of stoichiometric transition metal complexes in organic synthesis

Fletcher

Christie

2001

J. Chem. Soc., Perkin Trans. 1

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Introduction 2 Transition metal alkyl, alkenyl and allyl complexes in organic synthesis 2.1 Organozirconium-based methodology 2.2 Organotitanium-based methodology 2.3 Organoiron complexes 3 Group IV transition metal carbenes in organic synthesis 4 2 -Complexes in organic synthesis 5 3 -Complexes in organic synthesis 6 4 -Complexes in organic synthesis 7 5 -Complexes in organic synthesis 8 6 -Complexes in organic synthesis 9 Pauson-Khand reaction 10 References Scheme 1 Scheme 2

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“…Fp-substituted enones and enals undergo cyclocarbonylations on treatment with metal hydrides or metal alkyls to provide g-lactones (Scheme 1.15) [45]. Similarly, electron-rich primary amines afford dihydropyrrolones with iron-substituted (Z)-enals in the presence of titanium tetrachloride and triethylamine [46].…”

Section: Acyl-and Carbene-iron Complexesmentioning

confidence: 99%

Iron Complexes in Organic Chemistry

Бауер¹,

Knölker²

2008

Iron Catalysis in Organic Chemistry

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Catalysis is an important field in both academic and industrial research because it leads to more efficient reactions in terms of energy consumption and waste production. The common feature of these processes is a catalytically active species which forms reactive intermediates by coordination of an organic ligand and thus decreases the activation energy. Formation of the product should occur with regeneration of the catalytically active species. The efficiency of the catalyst can be described by its turnover number, providing a measure of how many catalytic cycles are passed by one molecule of catalyst.For efficient regeneration, the catalyst should form only labile intermediates with the substrate. This concept can be realized using transition metal complexes because metal-ligand bonds are generally weaker than covalent bonds. The transition metals often exist in different oxidation states with only moderate differences in their oxidation potentials, thus offering the possibility of switching reversibly between the different oxidation states by redox reactions.Many transition metals have been applied as catalysts for organic reactions [1]. So far, iron has not played a dominant role in catalytic processes. Organoiron chemistry was started by the discovery of pentacarbonyliron in 1891, independently by Mond [2] and Berthelot [3]. A further milestone was the report of ferrocene in 1951 [4]. Iron catalysis came into focus by the Reppe synthesis [5]. Kochi and coworkers published in 1971 their results on the iron-catalyzed crosscoupling of Grignard reagents with organic halides [6]. However, cross-coupling reactions became popular by using the late transition metals nickel and palladium. More recently, the increasing number of reactions using catalytic amounts of iron complexes indicates a renaissance of this metal in catalysis. This chapter describes applications of iron complexes in organic chemistry and thus paves the way for an understanding of iron catalysis.

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Synthesis of 5-Substituted α,β-Butenolides by Iron-promoted Intramolecular Cyclocarbonylation: Addition of Organometallic Reagents to Iron-substituted Enals

Abstract: Reactions of organolithium and Grignard reagents with cyclic [h 5 -C 5 H 5 (CO) 2 Fe]-substituted enals provide a,b-butenolides by a reaction cascade involving an intramolecular cyclocarbonylation step.

Cited by 10 publications

References 4 publications

Palladium‐catalyzed carbonylative cyclization of 3‐bromoallyl alcohols leading to furan‐2(5H)‐ones

Palladium‐catalyzed carbonylative cyclization of 3‐bromoallyl alcohols leading to furan‐2(5H)‐ones

Applications of stoichiometric transition metal complexes in organic synthesis

Iron Complexes in Organic Chemistry

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