Abstract
An excellent candidate as a proton substitute in man-made organic reactions is a Lewis acid. The goal of the research was to engineer an artificial proton of a special shape, which could be utilized as an effective tool for chemical reactions, by harnessing the high reactivity of the metal atom towards a variety of functional groups. Such a concept was initially researched by examining the influence of a specially designed organometallic reagent on a typical organic reaction. Michael addition of simple organolithium and magnesium reagent to aromatic aldehydes in the presence of a bulky organoaluminum reagent is described as an example of the concept. The successful discrimination observed led to examine the more intricate question of enantioface differentiation. A variety of Lewis acid reagents were utilized for Diels-Alder, aldol, and ene reactions with high enantioselectivities. The origins of the selectivity of these reactions are discussed. The review describes these points with a variety of designer Lewis acids selected to illustrate the utility of the concept.
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Yamamoto, H., Yanagisawa, A., Ishihara, K., Saito, S. (1999). Designer Lewis Acids for Selective Organic Synthesis. In: Scolastico, C., Nicotra, F. (eds) Current Trends in Organic Synthesis. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4801-0_8
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DOI: https://doi.org/10.1007/978-1-4615-4801-0_8
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