Jieping Zhu

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An unprecedent asymmetric catalytic benzilic amide rearrangement for the synthesis of a,a-disubstituted piperazinones is reported. The reaction proceeds via a domino [4+1] imidazolidination/formal 1,2-nitrogen shift/1,2-aryl or alkyl migration sequence, employing readily available vicinal tricarbonyl compounds and 1,2-diamines as starting materials. This approach provides an efficient access to chiral C3-disubsituted piperazin-2-ones with high enantiocontrol, which are exceedingly difficult to access from the existing synthetic methodologies. The observed enantioselectivity was proposed to be controlled by dynamic kinetic resolution in the 1,2-aryl/alkyl migration step. The resulting densely functionalized products are versatile building blocks to bioactive natural products, drug molecules and their analogues.

WILEY-V C H VERLAG GMBH2023

Asymmetric Construction of α,α‐Disubstituted Piperazinones Enabled by Benzilic Amide Rearrangement

Yuping He, Hua Wu, Jieping Zhu

An unprecedent asymmetric catalytic benzilic amide rearrangement for the synthesis of α,α-disubstituted piperazinones is reported. The reaction proceeds via a domino [4+1] imidazolidination/formal 1,2-nitro- gen shift/1,2-aryl or alkyl migration sequence, employing readily available vicinal tricarbonyl compounds and 1,2- diamines as starting materials. This approach provides an efficient access to chiral C3-disubsituted piperazin-2-ones with high enantiocontrol, which are exceedingly difficult to access from the existing synthetic method- ologies. The observed enantioselectivity was proposed to be controlled by dynamic kinetic resolution in the 1,2- aryl/alkyl migration step. The resulting densely function- alized products are versatile building blocks to bioactive natural products, drug molecules and their analogues.

2023

Asymmetric Synthesis of Enantioenriched Zigzag-Type Molecular Belts by Kinetic Resolution and Subsequent Transformations

Shuo Tong, Yang Zhang, Jieping Zhu

Asymmetric synthesis of enantioenriched zigzag-type molecular belts featuring copper/H8-binaphthol-catalyzed kinetic resolution of a resorcinarene derivative and subsequent transformations was developed. The acquired rigid and C4-symmetric belt exhibited remarkably enhanced photophysical and chiroptical properties in comparison to its conformationally fluxional macrocyclic precursor.

2023