Preparation of chiral ferrocenes by asymmetric synthesis or by kinetic resolution

Kagan, Henri B.; Riant, Olivier

doi:10.1016/s1874-5148(97)80006-1

Cited by 34 publications

(22 citation statements)

References 132 publications

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“…For example, routine chromatography of a simple methyl p -tolyl sulfoxide 20 ( Scheme 5 ) of 86% ee gave fractions of 20 , with the ee ranging from 99.5% (first) to 73% (last). The alarming SDEvC properties of chiral sulfoxides were further conveyed by Kagan et al in a series of successive publications [ 119 , 120 , 149 , 150 , 151 , 152 ], but the warning failed to influence the conservative mindset of the wider research community. Thus, out of some 700+ papers reporting catalytic enantioselective synthesis of chiral sulfoxides that have been published since the seminal work, only one review [ 153 ] and four research reports [ 154 , 155 , 156 , 157 ] cite Kagan’s work.…”

Section: Pedagogic Examples From the Literaturementioning

confidence: 99%

Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions

et al. 2021

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The purpose of this review is to highlight the necessity of conducting tests to gauge the magnitude of the self-disproportionation of enantiomers (SDE) phenomenon to ensure the veracity of reported enantiomeric excess (ee) values for scalemic samples obtained from enantioselective reactions, natural products isolation, etc. The SDE always occurs to some degree whenever any scalemic sample is subjected to physicochemical processes concomitant with the fractionation of the sample, thus leading to erroneous reporting of the true ee of the sample if due care is not taken to either preclude the effects of the SDE by measurement of the ee prior to the application of physicochemical processes, suppressing the SDE, or evaluating all obtained fractions of the sample. Or even avoiding fractionation altogether if possible. There is a clear necessity to conduct tests to assess the magnitude of the SDE for the processes applied to samples and the updated and improved recommendations described herein cover chromatography and processes involving gas-phase transformations such as evaporation or sublimation.

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Section: Pedagogic Examples From the Literaturementioning

confidence: 99%

Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions

et al. 2021

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“…Although, planar chirality has received much less attention than the other elements of chirality (centres and axes), a wide variety of ferrocenyl ligands with planar chirality is known to date. Since the pioneering work of Ugi [ 50 ], several 1,2-disubsituted ferrocenes have been synthesised and the role of additional stereogenic centres has been discussed [ 28 , 51 , 52 , 53 , 54 , 55 , 56 , 57 ]. Among them, JOSIPHOS type ligands have attracted tremendous attention because their successful application in industrial synthesis of ( S )-metolachlor, (+)-biotin and (+)- cis -methyldihydrojasmonate and it has stimulated intense studies in synthesis and applications of this kind of ligands [ 58 , 59 , 60 , 61 , 62 ].…”

Section: Diphosphine Ligands In Asymmetric Allylic Alkylation Reacmentioning

confidence: 99%

Recent Advances in the Application of Chiral Phosphine Ligands in Pd-Catalysed Asymmetric Allylic Alkylation

2011

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One of the most powerful approaches for the formation of simple and complex chiral molecules is the metal-catalysed asymmetric allylic alkylation. This reaction has been broadly studied with a great variety of substrates and nucleophiles under different reaction conditions and it has promoted the synthesis of new chiral ligands to be evaluated as asymmetric inductors. Although the mechanism as well as the active species equilibria are known, the performance of the catalytic system depends on the fine tuning of factors such as type of substrate, nucleophile nature, reaction medium, catalytic precursor and type of ligand used. Particularly interesting are chiral phosphines which have proved to be effective asymmetric inductors in several such reactions. The present review covers the application of phosphine-donor ligands in Pd-catalysed asymmetric allylic alkylation in the last decade.

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“…Since the first monograph reported by Hayashi in 1995 on the synthesis and applications of chiral ferrocenes in asymmetric catalysis,10 a set of reports by Kagan,11 Richards,12 Togni,13 Santelli,14 and Hou15 covering different aspects of chiral ferrocene ligands have been published. Furthermore, the reviews of Lemaire16a and Guiry16b,c on chiral nitrogen‐containing ligands include the case of ferrocenyl ligands bearing nitrogen donor atoms.…”

Section: Introductionmentioning

confidence: 99%

Recent Applications of Chiral Ferrocene Ligands in Asymmetric Catalysis

2006

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Despite the impressive progress achieved in asymmetric catalysis during the last decade, an increasing number of new catalysts, ligands, and applications are reported every year to satisfy the need to embrace a wider range of reactions and to improve the efficiency of existing processes. Because of their availability, unique stereochemical aspects, and wide variety of coordination modes and possibilities for the fine-tuning of the steric and electronic properties, ferrocene-based ligands constitute one of the most versatile ligand architectures in the current scenario of asymmetric catalysis. Over the last few years ferrocene catalysts have been successfully applied in an amazing variety of enantioselective processes. This Review documents these recent advances, with special emphasis on the most innovative asymmetric processes and the development of novel, efficient types of ferrocene ligands.

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Preparation of chiral ferrocenes by asymmetric synthesis or by kinetic resolution

Cited by 34 publications

References 132 publications

Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions

Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions

Recent Advances in the Application of Chiral Phosphine Ligands in Pd-Catalysed Asymmetric Allylic Alkylation

Recent Applications of Chiral Ferrocene Ligands in Asymmetric Catalysis

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