Recent advances and applications of iridium-catalysed asymmetric allylic substitution.

Recent advances and applications of iridium-catalysed asymmetric allylic substitution.

Organic & biomolecular chemistry (2012-03-13)

Paolo Tosatti, Adam Nelson, Stephen P Marsden

RESUMEN

Since their discovery in 1997, iridium-catalysed asymmetric allylic substitutions have been developed into a broadly applicable tool for the synthesis of chiral building blocks via C-C and C-heteroatom bond formation. The remarkable generality of these reactions and the high levels of regio- and enantioselectivity that are usually obtained in favour of the branched products have been made possible by a thorough investigation of the catalyst system and its mode of action. Therefore, today the Ir-catalysed asymmetric allylic substitution is a powerful reaction in the organic chemist's repertoire and has been used extensively for several applications. This article aims to provide an overview of the development of iridium catalysts derived from an Ir salt and a chiral phosphoramidite and their application to the enantioselective synthesis of natural products and biologically relevant compounds.

MATERIALES

Referencia del producto

Marca

Descripción del producto

209686

Sigma-Aldrich

Iridium, powder, 99.9% trace metals basis

357324

Sigma-Aldrich

Iridium, foil, thickness 0.25 mm, 99.9% trace metals basis

449229

Sigma-Aldrich

Iridium, evaporation slug, diam. × L 0.6 cm × 1.2 cm, 99.9% trace metals basis

GF43204834

Iridium, wire reel, 0.5m, diameter 0.5mm, as drawn, 99.9%

GF25136490

Iridium, wire reel, 0.5m, diameter 0.38mm, as drawn, 99.9%

GF10109629

Iridium, rod, 25mm, diameter 3.0mm, as drawn, 99.9%

GF96543209

Iridium, foil, 25x25mm, thickness 0.125mm, as rolled, 99.9%

GF51827328

Iridium, rod, 25mm, diameter 2.0mm, as drawn, 99.9%

GF92005220

Iridium, rod, 50mm, diameter 2.0mm, as drawn, 99.9%

GF35631200

Iridium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.9%

GF35321172

Iridium, rod, 50mm, diameter 3.0mm, as drawn, 99.9%

GF22425375

Iridium, wire reel, 0.05m, diameter 0.8mm, as drawn, 99.9%

GF26117490

Iridium, wire, straight, 100mm, diameter 0.5mm, as drawn, 99.9%

GF98486982

Iridium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%

GF20836425

Iridium, foil, 0.025m coil, thickness 0.05mm, coil width .5mm, as rolled, 99.9%

GF63698305

Iridium, microfoil, disks, 10mm, thinness 0.1μm, specific density 224μg/cm², permanent mylar 3.5μm support, 99.9%

GF86062923

Iridium, microfoil, disks, 25mm, thinness 0.1μm, specific density 224μg/cm², permanent mylar 3.5μm support, 99.9%

GF26409247

Iridium, wire reel, 0.1m, diameter 0.15mm, as drawn, 99.9%

GF97286428

Iridium, wire reel, 0.05m, diameter 0.1mm, as drawn, 99.9%

GF17748894

Iridium, wire reel, 1m, diameter 0.125mm, as drawn, 99.9%

GF15807900

Iridium, foil, 0.1m coil, thickness 0.05mm, coil width .5mm, as rolled, 99.9%

GF07858974

Iridium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.9%

GF06583394

Iridium, wire reel, 0.1m, diameter 0.075mm, as drawn, 99.9%

GF30370924

Iridium, wire reel, 0.2m, diameter 0.125mm, as drawn, 99.5%

GF26305130

Iridium, wire reel, 0.2m, diameter 0.125mm, as drawn, 99.9%

GF00883739

Iridium, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.9%

GF10466760

Iridium, wire reel, 0.3m, diameter 0.5mm, as drawn, 99.9%

GF18611276

Iridium, wire reel, 2m, diameter 0.125mm, as drawn, 99.9%

GF05163904

Iridium, wire, straight, 50mm, diameter 1.0mm, as drawn, 99.9%

GF68849544

Iridium, wire reel, 0.05m, diameter 2.0mm, as drawn, 99.9%