Dynamic Kinetic Resolution of Flavonoids via Asymmetric Allylic Alkylation: Construction of Two Contiguous Stereogenic Centers on Nucleophiles

The extension of racemization strategies of dynamic kinetic resolution in organic synthesis is a longstanding challenge, especially racemizing two or more stereogenic centers simultaneously. Through the combination of a palladium-catalyzed asymmetric allylic alkylation and a base-promoted retro-oxa-...

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Bibliographic Details
Published inACS catalysis Vol. 11; no. 21; pp. 12859 - 12863
Main Authors Liu, Li-Xia, Huang, Wen-Jun, Xie, Qing-Xian, Wu, Bo, Yu, Chang-Bin, Zhou, Yong-Gui
Format Journal Article
LanguageEnglish
Published American Chemical Society 05.11.2021
Subjects
retro-oxa-Michael addition
palladium catalysis
DKR
asymmetric allylic alkylation
flavonoids
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ISSN2155-5435
2155-5435
DOI10.1021/acscatal.1c03732

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Summary:The extension of racemization strategies of dynamic kinetic resolution in organic synthesis is a longstanding challenge, especially racemizing two or more stereogenic centers simultaneously. Through the combination of a palladium-catalyzed asymmetric allylic alkylation and a base-promoted retro-oxa-Michael addition, a dynamic kinetic resolution of 2,3-disubstituted flavonoids was achieved with up to 99% enantioselectivities, and two contiguous stereocenters (including a quaternary stereogenic center) were constructed simultaneously on the nucleophile flavonoids. The key feature of the reaction was a base-promoted retro-oxa-Michael addition for fast racemization of two stereogenic centers on the nucleophiles, which can pave the way to developing asymmetric reactions of flavonoids through dynamic kinetic resolution.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.1c03732