Stereodivergent 1,3-difunctionalization of alkenes by charge relocation

Bogdan R. Brutiu, Giulia Iannelli, Margaux Riomet, Daniel Kaiser and Nuno Maulide ()
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Bogdan R. Brutiu: University of Vienna
Giulia Iannelli: University of Vienna
Margaux Riomet: University of Vienna
Daniel Kaiser: University of Vienna
Nuno Maulide: University of Vienna

Nature, 2024, vol. 626, issue 7997, 92-97

Abstract: Abstract Alkenes are indispensable feedstocks in chemistry. Functionalization at both carbons of the alkene—1,2-difunctionalization—is part of chemistry curricula worldwide1. Although difunctionalization at distal positions has been reported2–4, it typically relies on designer substrates featuring directing groups and/or stabilizing features, all of which determine the ultimate site of bond formation5–7. Here we introduce a method for the direct 1,3-difunctionalization of alkenes, based on a concept termed ‘charge relocation’, which enables stereodivergent access to 1,3-difunctionalized products of either syn- or anti-configuration from unactivated alkenes, without the need for directing groups or stabilizing features. The usefulness of the approach is demonstrated in the synthesis of the pulmonary toxin 4-ipomeanol and its derivatives.

Date: 2024
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DOI: 10.1038/s41586-023-06938-0

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