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Issue 7, 2007
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Iridium-catalysed asymmetricallylic substitutions

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Abstract

Ir-Catalysed allylic substitution is supplementing the traditional Pd-catalysed variant. With simple, easily available monosubstituted allylic acetates and carbonates as substrates, Ir catalysts generally favour chiral, branched products, while Pd catalysts typically give rise to linear, achiral products. With phosphorus amidites as ligands, regioselectivities >10 : 1 and enantiomeric excess in the range 95–99 %ee are currently routinely achieved. A broad range of nucleophiles can be employed: for example stabilised carbanions, amines including their sulfonyl- and diacyl-derivatives, phenolates and alkoxides. A few applications, based on combinations of the allylic substitution and ring closing metathesis, indicate considerable potential of the method for the synthesis of biologically active compounds.

Graphical abstract: Iridium-catalysed asymmetricallylic substitutions

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Publication details

The article was received on 29 Sep 2006, accepted on 08 Nov 2006 and first published on 06 Dec 2006


Article type: Feature Article
DOI: 10.1039/B614169B
Chem. Commun., 2007, 675-691

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    Iridium-catalysed asymmetricallylic substitutions

    G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies and R. Weihofen, Chem. Commun., 2007, 675
    DOI: 10.1039/B614169B

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