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Steric parameters in the Ir-catalyzed regio- and diastereoselective isomerization of primary allylic alcohols.

Organic letters (2013-11-14)
Houhua Li, Clément Mazet
ABSTRACT

The iridium-catalyzed diastereo- and regioselective isomerization of primary allylic alcohols using Crabtree's catalyst or sterically modified analogs is reported. The importance of the size of the substituents on either the substrates or the catalysts has been rationalized by linear free energy relationships.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Allyl alcohol, ≥99%
Sigma-Aldrich
Iridium, powder, 99.9% trace metals basis
Sigma-Aldrich
Allyl alcohol, ≥98.5%
Sigma-Aldrich
Iridium, wire, diam. 0.15 mm, 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, black, powder, −200 mesh, ≥99% trace metals basis
Sigma-Aldrich
Iridium, foil, thickness 0.25 mm, 99.9% trace metals basis
Sigma-Aldrich
Allyl alcohol, ≥98.5%