1253889-39-2Relevant articles and documents
Enantioselective synthesis of 1-vinyltetrahydroisoquinolines through palladium-catalysed intramolecular allylic amidation with chiral PhthalaPhos ligands
Pignataro, Luca,Marelli, Enrico,Gennari, Cesare,Ferraccioli, Raffaella
, p. 844 - 850 (2014/06/23)
The PhthalaPhos ligands, chiral BINOL monophosphites endowed with a phthalamide group, have been screened in the synthesis of 1- vinyltetrahydroisoquinolines by intramolecular palladium-catalysed asymmetric allylic amidation (AAA) of achiral tosylamidocarbonates. Identification of the best ligand followed by optimisation of the reaction conditions allowed the desired product to be obtained with up to 83% ee. Remarkably, the reaction is stereoconvergent, affording the same enantiomer of the desired product regardless of the geometry of the allylic carbonate's double bond, which allows, in principle, the use of E/Z mixtures.
Phthalaphos: Chiral supramolecular ligands for enantioselective rhodium-catalyzed hydrogenation reactions
Pignataro, Luca,Carboni, Stefano,Civera, Monica,Colombo, Raffaele,Piarulli, Umberto,Gennari, Cesare
supporting information; experimental part, p. 6633 - 6637 (2010/10/21)
Interligand hydrogen bonding of chiral monodentate phosphite ligands bearing H-bond donor and acceptor groups leads to formation of supramolecular bidentate ligands, rhodium complexes of which (see picture) afford excellent enantiomeric excesses in catalyzed hydrogenation of classical benchmark and industrially relevant substrates. cod=1,5-cyclooctadiene.