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Asymmetric Allylic Substitutions Using Organometallic Reagents

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Progress in Enantioselective Cu(I)-catalyzed Formation of Stereogenic Centers

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 58))

Abstract

This chapter summarises recent progress in Cu-catalysed asymmetric allylic alkylation (AAA) with organometallic compounds, including Grignard, organolithium, organoaluminium, organozinc and organozirconium reagents. New reaction conditions and chiral ligands that improve these transformations or allow to overcome previous limitations associated with chemo-, regio- and enantioselectivities will be described. Moreover, a description of new ligands and conditions for the introduction of previously elusive nucleophiles, such as highly reactive organolithium compounds, is included together with a brief mechanistic discussion. Additionally, new challenging substrates which provide densely functionalised building blocks, as well as new synthetic applications that take advantage of the terminal olefin formed in these reactions, will be described.

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Authors and Affiliations

  1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands

    Valentín Hornillos, Jean-Baptiste Gualtierotti & Ben L. Feringa

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  1. Valentín Hornillos
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  2. Jean-Baptiste Gualtierotti
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  3. Ben L. Feringa
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Correspondence to Ben L. Feringa .

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  1. Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands

    Syuzanna R. Harutyunyan

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Hornillos, V., Gualtierotti, JB., Feringa, B.L. (2016). Asymmetric Allylic Substitutions Using Organometallic Reagents. In: Harutyunyan, S. (eds) Progress in Enantioselective Cu(I)-catalyzed Formation of Stereogenic Centers. Topics in Organometallic Chemistry, vol 58. Springer, Cham. https://doi.org/10.1007/3418_2015_165

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