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

ACS Catal. 2022 Sep 2;12(17):10887-10893. doi: 10.1021/acscatal.2c03158. Epub 2022 Aug 22.

ABSTRACT

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.

PMID:36082052 | PMC:PMC9442582 | DOI:10.1021/acscatal.2c03158

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