Issue 20, 2023

Asymmetric hydrogenation of all-carbon tetrasubstituted α-acylpyrazole-β-alkyl cycloalkenes

Abstract

Many bioactive molecules contain ring frameworks bearing 1,2-contiguous cis-stereocenters, but preparing such frameworks through asymmetric hydrogenation remains challenging. Here we report an Ir-catalyzed asymmetric hydrogenation of tetrasubstituted α-acylpyrazole-β-alkyl cycloalkenes to give 1,2-cis carbo- or heterocycles in yields up to 99% with enantioselectivities up to 99% ee. The acylpyrazole motif serves as a key directing group by coordinating the active Ir-complex with the alkene moiety. This work provides an efficient solution to the longstanding challenge of asymmetric hydrogenation of all-carbon tetrasubstituted β-alkyl cycloalkenes, which should be useful for the synthesis of bioactive molecules.

Graphical abstract: Asymmetric hydrogenation of all-carbon tetrasubstituted α-acylpyrazole-β-alkyl cycloalkenes

Supplementary files

Article information

Article type
Research Article
Submitted
31 jul 2023
Accepted
27 ago 2023
First published
29 ago 2023

Org. Chem. Front., 2023,10, 5070-5075

Asymmetric hydrogenation of all-carbon tetrasubstituted α-acylpyrazole-β-alkyl cycloalkenes

M. Zhang, P. Cui, K. Zhang, Z. Shi, X. Cheng, X. Ji, H. Song, B. Ke and Y. Qin, Org. Chem. Front., 2023, 10, 5070 DOI: 10.1039/D3QO01196H

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