Chiral phosphinoferrocene carboxamides with amino acid substituents as ligands for Pd-catalysed asymmetric allylic substitutions. Synthesis and structural characterisation of catalytically relevant Pd complexes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F11%3A10101070" target="_blank" >RIV/00216208:11310/11:10101070 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1039/c1dt11230a" target="_blank" >http://dx.doi.org/10.1039/c1dt11230a</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c1dt11230a" target="_blank" >10.1039/c1dt11230a</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Chiral phosphinoferrocene carboxamides with amino acid substituents as ligands for Pd-catalysed asymmetric allylic substitutions. Synthesis and structural characterisation of catalytically relevant Pd complexes

Popis výsledku v původním jazyce

An extensive series of chiral amino acid amides prepared from 1'-(diphenylphosphino)ferrocene-1-carboxylic acid (Hdpf) or its planar-chiral isomer, 2-(diphenylphosphino)ferrocene-1-carboxylic acid, have been tested as ligands for Pd-catalysed asymmetricallylic substitution reactions. In alkylation of 1,3-diphenylallyl acetate as a model substrate with dimethyl malonate the ligands performed well in terms of both reaction rate and enantioselectivity, achieving up to 98% ee. In contrast, the reactions ofthe same substrate with other nucleophiles proceeded either slowly and with poor ee's (amination with benzylamine) or not at all (etherification with benzyl alcohol). In order to rationalise the influence of the ligand structure on the reaction course,three model complexes, viz. [(h3-methallyl)PdCl(L-kP)], [(h3-methallyl)Pd(L-k2O,P)]ClO4 and [(h3-methallyl)Pd(L-kP)2]ClO4 have been prepared from the achiral amide Ph2PfcCONHCH2CO2Me (L; fc = ferrocene-1,1'-diyl) and structurally characte

Název v anglickém jazyce

Chiral phosphinoferrocene carboxamides with amino acid substituents as ligands for Pd-catalysed asymmetric allylic substitutions. Synthesis and structural characterisation of catalytically relevant Pd complexes

Popis výsledku anglicky

An extensive series of chiral amino acid amides prepared from 1'-(diphenylphosphino)ferrocene-1-carboxylic acid (Hdpf) or its planar-chiral isomer, 2-(diphenylphosphino)ferrocene-1-carboxylic acid, have been tested as ligands for Pd-catalysed asymmetricallylic substitution reactions. In alkylation of 1,3-diphenylallyl acetate as a model substrate with dimethyl malonate the ligands performed well in terms of both reaction rate and enantioselectivity, achieving up to 98% ee. In contrast, the reactions ofthe same substrate with other nucleophiles proceeded either slowly and with poor ee's (amination with benzylamine) or not at all (etherification with benzyl alcohol). In order to rationalise the influence of the ligand structure on the reaction course,three model complexes, viz. [(h3-methallyl)PdCl(L-kP)], [(h3-methallyl)Pd(L-k2O,P)]ClO4 and [(h3-methallyl)Pd(L-kP)2]ClO4 have been prepared from the achiral amide Ph2PfcCONHCH2CO2Me (L; fc = ferrocene-1,1'-diyl) and structurally characte

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CA - Anorganická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/LC06070" target="_blank" >LC06070: Struktura a syntetické aplikace komplexů přechodných kovů</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2011

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Dalton Transactions

ISSN

1477-9226

e-ISSN

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Svazek periodika

40

Číslo periodika v rámci svazku

44

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

11748-11757

Kód UT WoS článku

000296776200014

EID výsledku v databázi Scopus

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