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Copper-Catalyzed Hydroalumination of Allenes with Diisobutylaluminum Hydride: Synthesis of Allylic Ketones with α-Quaternary Centers via Tandem Allylation/Oppenauer Oxidation

Sangback Lee, Sanghyun Lee and Yunmi Lee*

*Department of Chemistry, Kwangwoon University, Seoul 01897, Republic of Korea, Email:

S. Lee, S. Lee, Y. Lee, Org. Lett., 2020, 22, 5806-5810.

DOI: 10.1021/acs.orglett.0c01876

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A Cu-catalyzed hydroalumination of readily accessible allenes with diisobutylaluminum hydride provides allylaluminum reagents under mild reaction conditions. A subsequent tandem nucleophilic addition to aldehydes/Oppenauer oxidation enables a one-pot synthesis of allylic ketones with α-tertiary and α-quaternary centers.

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proposed mechanism

Key Words

Allylic Ketones, Oppenauer Oxidation

ID: J54-Y2020