Catalytic enantioselective addition of organometallics to unprotected carboxylic acids

Xingchen Yan and Syuzanna R. Harutyunyan ()
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Xingchen Yan: University of Groningen
Syuzanna R. Harutyunyan: University of Groningen

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Conjugate addition of organometallics to carbonyl based Michael acceptors is a widely used method that allows the building of new carbon-carbon (C-C) bonds and the introduction of chirality in a single step. However, conjugate additions to the simplest Michael acceptors, namely unprotected, unsaturated carboxylic acids, are considered to be prohibited by the fact that acid-base reactions overpower any other type of reactivity, including nucleophilic addition. Here we describe a transient protecting group strategy that allows efficient catalytic asymmetric additions of organomagnesium reagents to unprotected α,β-unsaturated carboxylic acids. This unorthodox pathway is achieved by preventing the formation of unreactive carboxylate salts by means of a reactive intermediate, allowing modifications of the carbon chain to proceed unhindered, while the stereochemistry is controlled with a chiral copper catalyst. A wide variety of β-chiral carboxylic acids, obtained with excellent enantioselectivities and yields, can be further transformed into valuable molecules through for instance catalytic decarboxylative cross-coupling reactions.

Date: 2019
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DOI: 10.1038/s41467-019-11345-z

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