Asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes by synergistic Pd/chiral primary amine catalysis

Chang You, Mingying Shi, Xueling Mi () and Sanzhong Luo ()
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Chang You: Tsinghua University
Mingying Shi: Beijing Normal University
Xueling Mi: Beijing Normal University
Sanzhong Luo: Tsinghua University

Nature Communications, 2023, vol. 14, issue 1, 1-7

Abstract: Abstract We herein describe an asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes with 1,3-enynes. A synergistic chiral primary amine/Pd catalyst was identified to facilitate the utilization of 1,3-enynes as atom-economic and achiral allene precursors. The synergistic catalysis enables the construction of all-carbon quaternary centers-tethered allenes bearing non-adjacent 1,3-axial central stereogenic centers in high level of diastereo- and enantio-selectivity. By switching the configurations of ligands and aminocatalysts, diastereodivergence can be achieved and any of the four diastereoisomers can be accessed in high diastereo- and enantio- selectivity.

Date: 2023
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DOI: 10.1038/s41467-023-38488-4

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