4.7 Article

Asymmetric Transfer Hydrogenation of 2,3-Disubstituted Flavanones through Dynamic Kinetic Resolution Enabled by RetroOxa-Michael Addition: Construction of Three Contiguous Stereogenic Centers

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 11, Pages 7521-7530

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00418

Keywords

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Funding

  1. National Natural Science Foundation of China [21871255, 21690074]
  2. K. C. Wong Education Foundation [GJTD-2020-08]
  3. Chinese Academy of Sciences

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In this study, a ruthenium-catalyzed asymmetric transfer hydrogenation of 2,3-disubstituted flavanones was developed. The reaction allowed for the construction of three contiguous stereocenters under basic conditions through a combination of dynamic kinetic resolution and retro-oxa-Michael addition. This method provided chiral flavanols with excellent enantioselectivities and diastereoselectivities.
A ruthenium-catalyzed asymmetric transfer hydrogenation of 2,3-disubstituted flavanones was developed for the construction of three contiguous stereocenters under basic conditions through a combination of dynamic kinetic resolution and retro-oxa-Michael addition, giving chiral flavanols with excellent enantioselectivities and diastereoselectivities. The reaction proceeded via a base-catalyzed retro-oxa-Michael addition to racemize two stereogenic centers simultaneously in concert with a highly enantioselective ketone transfer hydrogenation step. The asymmetric transfer hydrogenation could be achieved at gram scale without loss of the activity and enantioselectivity.

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