Enantioselective Redox-Neutral Coupling of Aldehydes and Alkenes by an Iron-Catalyzed “Catch–Release” Tethering Approach

The reductive coupling of aldehydes and alkenes is an emerging technology that holds the potential to reinvent carbonyl addition chemistry. However, existing enantioselective methods are limited to form “branched” products. Herein, we present a directed enantio- and diastereoselective alkylation of...

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Veröffentlicht in:Journal of the American Chemical Society 2019-01, Vol.141 (1), p.143-147
Hauptverfasser: Li, Jing, Preinfalk, Alexander, Maulide, Nuno
Format: Artikel
Sprache:eng
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Zusammenfassung:The reductive coupling of aldehydes and alkenes is an emerging technology that holds the potential to reinvent carbonyl addition chemistry. However, existing enantioselective methods are limited to form “branched” products. Herein, we present a directed enantio- and diastereoselective alkylation of aldehydes with simple olefins to selectively yield linear coupling products. This is achieved by redox-neutral remote functionalization, whereby a tethering “catch–release” strategy decisively solves the key problems of reactivity and selectivity.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.8b12242