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Lewis Acid-Catalysed Aldol Reactions

Titanium Lewis Acids

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Aldol Reactions

Mukaiyama and coworkers were the first to demonstrate the utility of titanium Lewis acids in aldol additions. In their initial experiments they used titanium(IV) chloride in catalytic amounts in aldol reactions with silyl enol ethers.1,2,3 These initial findings were subsequently generalized and optimized in the following time. Numerous publications described the design of highly effective chiral titanium Lewis acids in enantioselective Mukaiyama reactions. Ab initio calculations were employed to investigate the mechanism of Lewis acid-catalysed Mukaiyama reactions.4 This important development was the object of several comprehensive revi ews.5,6,7,8,9,10,11,12,13,14,15,16 For that reasons only selected and latest examples should illustrate this development.

Optical active binaphthol is one of the most frequently applied ligands in the synthesis of chiral titanium Lewis acids. Reetz and coworkers were the first to report enantioselective Mukaiyama aldol reactions catalysed by modified BINOL—titanium(IV) complexes.17 These findings were optimized for acetate aldol additions. When used with 5 mol% of this so-called Mikami catalyst18 the expected β-hydroxy carboxylic esters were obtained with a high degree of enantioselectivity (Scheme 3.1.1.1).19

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Editor information

Editors and Affiliations

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

    Rainer Mahrwald

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(2009). Lewis Acid-Catalysed Aldol Reactions. In: Mahrwald, R. (eds) Aldol Reactions. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8701-1_8

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