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  • Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency.

Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency.

Chemical communications (Cambridge, England) (2009-12-22)
Soo Bong Han, In Su Kim, Michael J Krische
ABSTRACT

Existing methods for enantioselective carbonyl allylation, crotylation and tert-prenylation require stoichiometric generation of pre-metallated nucleophiles, and often employ stoichiometric chiral modifiers. Under the conditions of transfer hydrogenation employing an ortho-cyclometallated iridium C,O-benzoate catalyst, enantioselective carbonyl allylations, crotylations and tert-prenylations are achieved in the absence of stoichiometric metallic reagents or stoichiometric chiral modifiers. Moreover, under transfer hydrogenation conditions, primary alcohols function dually as hydrogen donors and aldehyde precursors, enabling enantioselective carbonyl addition directly from the alcohol oxidation level.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Iridium, black, powder, −200 mesh, ≥99% trace metals basis
Sigma-Aldrich
Iridium, wire, diam. 0.15 mm, 99.9% trace metals basis
Sigma-Aldrich
Iridium, powder, 99.9% trace metals basis
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
Iridium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%
Iridium, foil, 0.05m coil, thickness 0.05mm, coil width .5mm, as rolled, 99.9%
Iridium, foil, 25x25mm, thickness 0.25mm, as rolled, 99.9%
Iridium, rod, 50mm, diameter 2.0mm, as drawn, 99.9%
Iridium, foil, 0.025m coil, thickness 0.05mm, coil width .5mm, as rolled, 99.9%
Iridium, wire reel, 0.2m, diameter 0.125mm, as drawn, 99.9%
Iridium, rod, 50mm, diameter 3.0mm, as drawn, 99.9%
Iridium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.9%
Iridium, wire reel, 0.2m, diameter 0.075mm, as drawn, 99.9%
Iridium, wire reel, 0.05m, diameter 0.1mm, as drawn, 99.9%
Iridium, wire reel, 0.2m, diameter 0.1mm, as drawn, 99.9%
Iridium, wire reel, 0.1m, diameter 0.125mm, as drawn, 99.9%
Iridium, wire reel, 0.1m, diameter 0.25mm, as drawn, 99.9%
Iridium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.9%
Iridium, wire reel, 0.2m, diameter 0.15mm, as drawn, 99.9%
Iridium, wire reel, 0.1m, diameter 0.177mm, as drawn, 99.9%
Iridium, microfoil, disks, 25mm, thinness 0.1μm, specific density 224μg/cm2, permanent mylar 3.5μm support, 99.9%
Iridium, wire reel, 0.1m, diameter 0.5mm, as drawn, 99.9%
Iridium, wire reel, 0.2m, diameter 0.125mm, as drawn, 99.5%
Iridium, wire reel, 0.05m, diameter 0.8mm, as drawn, 99.9%
Iridium, wire reel, 0.1m, diameter 0.2mm, as drawn, 99.9%
Iridium, rod, 25mm, diameter 2.0mm, as drawn, 99.9%
Iridium, wire reel, 0.05m, diameter 0.075mm, as drawn, 99.9%
Iridium, wire reel, 0.2m, diameter 0.177mm, as drawn, 99.9%
Iridium, wire reel, 0.1m, diameter 0.075mm, as drawn, 99.9%