Indenone synthesis. Improved synthetic protocol and effect of substitution on the intramolecular Friedel–Crafts acylation

Galatsis, Paul; Manwell, Jeffrey J.; Blackwell, James M.

doi:10.1139/v94-208

Cited by 34 publications

(15 citation statements)

References 2 publications

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“…Reaction with an organometallic nucleophile affords the cyclopropylcarbinol which, under Lewis acidic conditions, undergoes ring expansion to regioselectively substituted naphthalenes 185. A carbon label would be most conveniently introduced via the indenone from either [ 14 C]acetic acid or [ 14 C]benzaldehyde rather than from trimethylsilyldiazomethane (Scheme ) 186…”

Section: Ring Expansionmentioning

confidence: 99%

Synthetic approaches to regiospecifically mono‐ and dilabelled arenes

Gregson

Herbert

Row

2011

Labelled Comp Radiopharmac

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A variety of methods for the preparation of selectively mono-, di-or tri-labelled arenes are reviewed. The review concentrates on those for which the application to labelled synthesis has been demonstrated. Further methods, the application of which to labelled synthesis appears viable but which have not been reduced to practise, are included also. The available methods provide a range of substitution patterns.

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Section: Ring Expansionmentioning

confidence: 99%

Synthetic approaches to regiospecifically mono‐ and dilabelled arenes

Gregson

Herbert

Row

2011

Labelled Comp Radiopharmac

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“…[41] 3-Hydroxy-3-(4'-methoxyphenyl)propanoic acid (3c): The 1 H and 13 C NMR spectra match those reported in the literature. [42] 3-Hydroxy-3-(2'-methylphenyl)propanoic acid (3d): [43] 3-Hydroxy-2-methyl-3-phenylpropanoic acid (3f): For purification, KHCO 3 was added, and EtOAc was used to extract unreacted ketone and any methyl ester. The aqueous layer was acidified to pH 1 using 1 M HCl, and the product was extracted into EtOAc.…”

Section: H Nmr Spectroscopymentioning

confidence: 99%

β‐Hydroxycarboxylic Acids from Simple Ketones by Carboxylation and Asymmetric Hydrogenation

2008

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We present a new asymmetric synthesis of b-hydroxycarboxylic acids from ketones, performed by carboxylation using CO 2 followed by asymmetric hydrogenation. First, the carboxylation of ketones gives b-ketocarboxylic acids. The effects of temperature, reaction time, and amount of 1,.0]undec-7-ene (DBU) promoter on the carboxylation were investigated. The DBU can be recycled. For the second step, the asymmetric hydrogenation of these b-ketocarboxylic acids, we determined the effect of solvent choice, H 2 pressure, and substrate substitution. Hydrogenation yield and enantioselectivity are solvent-dependent, and the mechanism could proceed through hydrogenation of either the enol or the keto forms of the bound substrate. This synthesis is industrially advantageous due to the limited number of reactants required, their low-cost, and the potential for recycling unused materials.

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“…A great many methods have been developed for the preparation of these valuable compounds over the past few decades. Traditional methods to indenones usually suffer from harsh reaction conditions, multiple steps, and narrow substrate scope . In recent years, transition-metal-catalyzed construction of indenones has been intensively explored through the annulation of alkynes and ortho -functionalized aromatic aldehydes, esters, or nitriles, which has provided a new avenue for the efficient formation of indenones .…”

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confidence: 99%