Details

Autor(en) / Beteiligte

• Tsuji, Nobuya
• Kennemur, Jennifer L
• Buyck, Thomas
• Lee, Sunggi
• Prévost, Sébastien
• Kaib, Philip S J
• Bykov, Dmytro
• Farès, Christophe
• List, Benjamin

Titel

Activation of olefins via asymmetric Brønsted acid catalysis

Ist Teil von

• Science (American Association for the Advancement of Science), 2018-03, Vol.359 (6383), p.1501-1505

Ort / Verlag

United States: The American Association for the Advancement of Science

Erscheinungsjahr

2018

Link zum Volltext

Quelle

American Association for the Advancement of Science

Beschreibungen/Notizen

• The activation of olefins for asymmetric chemical synthesis traditionally relies on transition metal catalysts. In contrast, biological enzymes with Brønsted acidic sites of appropriate strength can protonate olefins and thereby generate carbocations that ultimately react to form natural products. Although chemists have recently designed chiral Brønsted acid catalysts to activate imines and carbonyl compounds, mimicking these enzymes to protonate simple olefins that then engage in asymmetric catalytic reactions has remained a substantial synthetic challenge. Here, we show that a class of confined and strong chiral Brønsted acids enables the catalytic asymmetric intramolecular hydroalkoxylation of unbiased olefins. The methodology gives rapid access to biologically active 1,1-disubstituted tetrahydrofurans, including (-)-Boivinianin A.