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The Asymmetric Phospho-Aldol Reaction. Past, Present and Future

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Book cover New Aspects in Phosphorus Chemistry II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 223))

Abstract

The phospho-aldol reaction is a well-known and increasingly exploited synthetic process for the construction of phosphorus-carbon bonds. The reaction, essentially a base-catalysed addition reaction between a hydrogen-phosphonate ester and a carbonyl substrate, affords alpha-(α)-functionalised phosphonate esters. Such molecular scaffolds offer considerable scope in medicinal chemistry as the basis for new enzyme inhibitors. Since the 1950s there have been many variants of the basic phospho-aldol reaction published for the stoichiometric synthesis of α-functionalised phosphonates, but most recently attention has shifted to the control of asymmetry in the transformation. It has been shown that the biological properties of α-functionalised phosphonates are influenced by their stereochemistry. This report summarises the developments in asymmetric catalytic variants of the phospho-aldol reaction tracing their evolution from early studies in the 1980s to the current day whilst attempting to suggest future advances within the context of growing applications in biomedical science.

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Authors and Affiliations

  1. School of Chemistry, University of Leeds, Woodhouse Lane, Leeds, LS2 9JT, UK

    Terence P. Kee & Tracy D. Nixon

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  1. Terence P. Kee
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  1. Laboratoire de Chimie de Coordination du CNRS, 205, route de Narbonne, 31077, Toulouse, Cedex 4, France

    Jean-Pierre Majoral (Directeur de Recherche) (Directeur de Recherche)

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Kee, T.P., Nixon, T.D. (2003). The Asymmetric Phospho-Aldol Reaction. Past, Present and Future. In: Majoral, JP. (eds) New Aspects in Phosphorus Chemistry II. Topics in Current Chemistry, vol 223. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-46100-0_2

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  • DOI: https://doi.org/10.1007/3-540-46100-0_2

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