Transition-metal mediated asymmetric synthesis. Part 3. Preparation and stereospecific alkylation of unsymmetrically substituted tricarbonyl(cyclohexadienyl)iron(1+) salts: an organometallic approach to the synthesis of carvone, cryptomerion, and bilobanone

Stephenson, G. R.

doi:10.1039/p19820002449

Cited by 21 publications

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TheBirch Reduction of Aromatic Compounds

Rabideau

Marcinow²

1992

Organic Reactions

134

138

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The reduction of aromatic compounds by alkali metals in liquid ammonia represents an important method for the preparation of partially unsaturated six‐membered rings. The reaction was discovered by Wooster and Godfrey, but the major development resulted from the efforts of A. J. Birch, and the reaction has since come to bear his name. Although a variety of metals can be used, the most common are sodium and lithium, and, to a lesser extent, potassium. Cosolvents such as ether or tetrahydrofuran (THF) are often used to improve solubility, and weak acids such as alcohols may be employed during the reaction as proton sources. The latter are necessary for the reduction of benzene and its unactivated derivatives. Improvement in experimental procedures by Wilds and Nelson, the application to polynuclear compounds by Hückel and later by Harvey, and the development of methods for the alkylation of the anions generated in this process (i.e., reductive alkylation) have made this reaction an important approach to the synthesis of a wide variety of organic compounds.

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TheBirch Reduction of Aromatic Compounds

Rabideau

Marcinow²

1992

Organic Reactions

134

138

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Polyfunctional Electrophilic Multihapto‐Organometallics for Organic Synthesis

Stephenson¹

2005

Handbook of Functionalized Organometallics

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Selective Synthesis and Reactivity of η⁵‐Arylcyclohexadienyliron Complexes

Owen¹,

Malkov²,

Palotai³

et al. 2007

Chemistry A European J

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A series of aryl-substituted cyclohexadienyliron complexes have been prepared by a general procedure that determines regioselectivity by correctly positioning leaving groups in the precursor complexes. The aryl groups at 1-C or 2-C have been shown to be omega directing by the study of reactions with a representative range of nucleophiles, and these regioselectivity properties have been related to the spectroscopic properties of the cationic cyclohexadienyliron complexes. A high level of electron-donating substituents on the arene, or switching between the [Fe(CO)3] and [Fe(CO)2PPh3] series, reduces the minor ipso pathway, improving regiocontrol. Placing opposed directing groups in the arylcyclohexadienyliron complexes reverts reactivity to the ipso pathway with stabilised enolate nucleophiles, and when the additional directing group reinforces the effect of the aryl group, the ipso pathway is stopped.

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Transition-metal mediated asymmetric synthesis. Part 3. Preparation and stereospecific alkylation of unsymmetrically substituted tricarbonyl(cyclohexadienyl)iron(1+) salts: an organometallic approach to the synthesis of carvone, cryptomerion, and bilobanone

Abstract: Die direkte Komplexierung des Cyclohexadiens (I) mit Fe(CO)5 im Überschuß lieferte den gewünschten Komplex (IIa) nur in geringer Menge im Gemisch mit den Komplexen (IIb)‐(IIg), die durch Demethoxylierung entstehen und chromatographisch getrennt werden können.

Cited by 21 publications

References 1 publication

TheBirch Reduction of Aromatic Compounds

TheBirch Reduction of Aromatic Compounds

Polyfunctional Electrophilic Multihapto‐Organometallics for Organic Synthesis

Selective Synthesis and Reactivity of η⁵‐Arylcyclohexadienyliron Complexes

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Transition-metal mediated asymmetric synthesis. Part 3. Preparation and stereospecific alkylation of unsymmetrically substituted tricarbonyl(cyclohexadienyl)iron(1+) salts: an organometallic approach to the synthesis of carvone, cryptomerion, and bilobanone

Abstract: Die direkte Komplexierung des Cyclohexadiens (I) mit Fe(CO)5 im Überschuß lieferte den gewünschten Komplex (IIa) nur in geringer Menge im Gemisch mit den Komplexen (IIb)‐(IIg), die durch Demethoxylierung entstehen und chromatographisch getrennt werden können.

Cited by 21 publications

References 1 publication

TheBirch Reduction of Aromatic Compounds

TheBirch Reduction of Aromatic Compounds

Polyfunctional Electrophilic Multihapto‐Organometallics for Organic Synthesis

Selective Synthesis and Reactivity of η5‐Arylcyclohexadienyliron Complexes

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Selective Synthesis and Reactivity of η⁵‐Arylcyclohexadienyliron Complexes