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Issue 4, 2018
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Catalytic nucleophilic ‘umpoled’ π-allyl reagents

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Abstract

After seminal Tsuji–Trost reactions (palladium catalyzed allylation of nucleophiles via π-allyl intermediates as electrophiles), the idea of reversal reactivity of π-allyl intermediates (i.e. π-allyl as nucleophiles) has been stated since the eighties. Thanks to different transition metal sources and the modification of their electronic environment through the use of additives and ligands, such ‘reactivity switch’ of π-allyl intermediates proved its powerfulness allowing high control in regio-, diastereo- and enantio-selectivities. These methodologies have thus emerged as efficient methods in the catalytic enantioselective allylation of carbonyl compounds and imines with a deep impact on natural product and/or drug elaboration. This tutorial review highlights the concept of ‘umpoled’ reactivity of π-allyl intermediates, relying on selected recent examples.

Graphical abstract: Catalytic nucleophilic ‘umpoled’ π-allyl reagents

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Article information


Submitted
16 Jun 2017
First published
11 Jan 2018

Chem. Soc. Rev., 2018,47, 1159-1173
Article type
Tutorial Review

Catalytic nucleophilic ‘umpoled’ π-allyl reagents

K. Spielmann, G. Niel, R. M. de Figueiredo and J. Campagne, Chem. Soc. Rev., 2018, 47, 1159
DOI: 10.1039/C7CS00449D

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