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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

ABSTRACT

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.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Iridium, powder, 99.9% trace metals basis

Iridium, wire reel, 0.05m, diameter 1.0mm, as drawn, 99.9%

Iridium, wire reel, 0.1m, diameter 0.38mm, as drawn, 99.9%

Iridium, wire reel, 0.025m, diameter 2.0mm, as drawn, 99.9%

Iridium, wire reel, 0.2m, diameter 0.1mm, as drawn, 99.9%

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

Iridium, wire reel, 0.1m, diameter 0.5mm, as drawn, 99.9%

Iridium, foil, 25x25mm, thickness 0.25mm, as rolled, 99.9%

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

Iridium, wire reel, 0.05m, diameter 0.075mm, as drawn, 99.9%

Iridium, wire reel, 0.2m, diameter 0.25mm, as drawn, 99.9%

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

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

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

Iridium, wire reel, 0.5m, diameter 0.075mm, as drawn, 99.9%

Iridium, wire reel, 1m, diameter 0.1mm, as drawn, 99.9%

Iridium, wire reel, 0.5m, diameter 0.125mm, as drawn, 99.5%

Iridium, wire reel, 0.5m, diameter 0.25mm, as drawn, 99.9%

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

Iridium, wire reel, 1m, diameter 0.25mm, as drawn, 99.9%

Iridium, wire reel, 0.5m, diameter 0.125mm, as drawn, 99.9%

Iridium, wire reel, 1m, diameter 0.15mm, as drawn, 99.9%

Iridium, wire, straight, 100mm, diameter 0.7mm, as drawn, 99.9%

Iridium, wire, straight, 50mm, diameter 0.7mm, as drawn, 99.9%

Iridium, wire reel, 0.1m, diameter 0.8mm, as drawn, 99.9%

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

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

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