Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes

Kieran Nicholson, Yuxuan Peng, Natalia Llopis, Dominic R. Willcox, Gary S. Nichol, Thomas Langer, Alejandro Baeza, Stephen P. Thomas

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

The diastereo- and enantioselective allylation of ketones remains a synthetic challenge, with transition metal catalysis offering the most applied methods. Here, a boron-catalyzed allylation of ketones with allenes is presented. Excellent yield, regioselectivity, and diastereoselectivity were found across functionalized substrates. The reaction was further developed to accommodate an enantioenriched boron catalyst and thus gave asymmetric ketone allylation in good yield, diastereoselectivity, and enantioselectivity. Mechanistic studies supported a hydroboration–allylation–transborylation pathway.
Original languageEnglish
Pages (from-to)10887-10893
JournalACS Catalysis
Early online date22 Aug 2022
DOIs
Publication statusE-pub ahead of print - 22 Aug 2022

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