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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Chiral benzo[2.2.1] α-hydroxyketones from a dirhodium(ii)/bisphosphine-catalyzed desymmetrization addition reaction
Shuming Zhan1, Chengyu Wang1, Longhui Duan1
1Department of Chemistry, University of Science and Technology of China 96 Jinzhai Road Hefei Anhui 230026 P. R. China.
Abstract:
The [2.2.1]-bridged bicyclic framework represents a privileged structural motif prevalent in numerous bioactive molecules and functional materials. The development of efficient synthetic methods for constructing these valuable architectures remains highly desirable. In this study, we report a dirhodium(ii)/bisphosphine-catalyzed desymmetrization reaction of benzobicyclo[2.2.1]heptane-2,3-diones with arylboronic acids. This transformation delivers enantioenriched benzo[2.2.1] α-hydroxy ketones with excellent enantioselectivity (up to 94% ee) across a diverse substrate scope. The synthetic utility of these chiral products is demonstrated through several transformations, including the preparation of a chiral phosphine.
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