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Copper Lewis Acids

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Aldol Reactions

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In 1996, chiral (pybox)Cu(II) complexes were employed as catalysts in highly enantioselective aldol additions for the first time. For comprehensive overviews of this development see Stanley and Sibi and others.1,2,3 The Mukaiyama aldol addition of (benzyloxy)acetaldehyde 2 is catalysed by chiral bis(oxazoline) Cu(OTf)2 6 and pyridyl bis(oxazoline) Cu(II) complex 7. Enantioselectivities are significantly lower for aldehydes nominally incapable of chelation (Scheme 3.1.4.1).4,5

This transformation can be extended to vinylogous substrates. Chan diene 8 and diene acetal 10 react with benzyloxyacetaldehyde to yield the expected δ-hydroxy compounds 9 and 11 with a high degree of enantioselectivity (Scheme 3.1.4.2).

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Editors and Affiliations

  1. Institute of Chemistry, Humboldt University, Brook Taylor Str. 2, Berlin, 12 489, Germany

    Rainer Mahrwald

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(2009). Copper Lewis Acids. In: Mahrwald, R. (eds) Aldol Reactions. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8701-1_11

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