Selective methods in organic synthesis

Projektinformationen

ID Finanzhilfevereinbarung: INTAS-93-1482

Projekt abgeschlossen

Startdatum 1 Oktober 1994

Enddatum 30 September 1995

Finanziert unter

• International Association for the promotion of cooperation with scientists from the independent states of the former Soviet Union (INTAS), 1993-

Gesamtkosten

Keine Daten

EU-Beitrag

€ 20 000,00

Koordiniert durch

Ecole Nationale Supérieure de Chimie de la Ville de Paris
France

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Verwertbare Ergebnisse

Selective methods in organic synthesis

Several methods of selective Csp2-C and Csp2-heteroatom bonds formation have been developed, among which is the hydrophosphorilation of terminal alkynes leading to α-substituted vinylphosphonates. Their subsequent asymmetric Ru(II) catalyzed homogeneous hydrogenation provides a new practical procedure for the enetioselective synthesis of α-substituted ethylphosphonic acids and esters (phosphorous analogues of well known non-steroidal anti-inflammatory drugs naproxen and ibuprofen). Arylation (SNAr and palladium-catalyzed cross-coupling) of wide range of substrates (carbanions, heterocycles, silylphosphines) have been studied. The products obtained are of interest as ligands for transition metal catalysis (secondary and tertiary P-chiral phosphines), potentially bioactive compounds (substituted α-arylmethylphosphonates) and organic sythons (1-N-arylated benzotriazoles). In each case the reaction conditions were found to obtain the high yield of the product. The synthesis of several tetraphosphines with bis-phosphine chelating moieties was carried out using Pd-catalyzed cross-coupling reaction and Pd-complexes of these ligands were obtained.