Citation: Xiangwei Ren, Hongli Wu, Mei Zhang, Wentao Zhao, Genping Huang. Origins of catalyst-controlled enantiodivergent hydroamination of enones with pyridazinones: A computational study[J]. Chinese Chemical Letters, ;2021, 32(9): 2769-2772. doi: 10.1016/j.cclet.2021.02.049 shu

Origins of catalyst-controlled enantiodivergent hydroamination of enones with pyridazinones: A computational study

Department of Chemistry, School of Science and Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, Tianjin 300072, China

wentao_zhao@tju.edu.cn

gphuang@tju.edu.cn

Received Date: 15 January 2021
Revised Date: 22 February 2021
Accepted Date: 23 February 2021
Available Online: 25 February 2021

Figures(4)

Density functional theory calculations have been performed to investigate the dipeptide phosphine-catalyzed hydroamination of enones with pyridazinones. The computations reveal that a number of the NH···O hydrogen-bonding interactions with the pyridazinone moiety and the C-H···O hydrogen-bonding interactions with the enone moiety are present in the enantioselectivity-determining Michael addition transition states. The experimentally-observed catalyst-controlled enantiodivergence is mainly attributed to the significant impact of the substituent of the amide moiety of the dipeptide phosphine on the relative strength of the NH···O hydrogen-bonding interactions, which was found to affect the Si face attack transition state, enabling the enantioselectivity switch upon change of chiral dipeptide phosphine catalyst.
- Dipeptide phosphine catalyst,
- Hydroamination,
- Mechanism,
- Selectivity,
- DFT calculations
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