Stereodivergent 1,3-difunctionalization of alkenes by charge relocation.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 38297174.
- Also identified by DOI 10.1038/s41586-023-06938-0 and PMC identifier 10830407.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
Alkenes are indispensable feedstocks in chemistry. Functionalization at both carbons of the alkene-1,2-difunctionalization-is part of chemistry curricula worldwide<sup>1</sup>. Although difunctionalization at distal positions has been reported<sup>2-4</sup>, it typically relies on designer substrates featuring directing groups and/or stabilizing features, all of which determine the ultimate site of bond formation<sup>5-7</sup>. 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.