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  • Title: Enhanced anti-diastereo- and enantioselectivity in alcohol-mediated carbonyl crotylation using an isolable single component iridium catalyst.
    Author: Gao X, Townsend IA, Krische MJ.
    Journal: J Org Chem; 2011 Apr 01; 76(7):2350-4. PubMed ID: 21375283.
    Abstract:
    The cyclometalated iridium complex (S)-I derived from [Ir(cod)Cl](2), 4-cyano-3-nitrobenzoic acid, allyl acetate, and (S)-SEGPHOS is conveniently isolated by precipitation or through conventional silica gel flash chromatography. This single-component precatalyst allows alcohol mediated carbonyl crotylations to be performed at significantly lower temperature, resulting in enhanced levels of anti-diastereo- and enantioselectivity. Most significantly, the chromatographically isolated precatalyst (S)-I enables carbonyl crotylations that are not possible under previously reported conditions involving in situ generation of (S)-I.
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