DFT Study on Zr-Catalyzed Alkene Hydroaminoalkylation: Origin of Regioselectivity, Diastereoselectivity, and Influence of Substrate

A DFT study was carried out to investigate a zirconium-catalyzed hydroaminoalkylation of alkenes with N-silylated benzylamine. A global reactivity index (GRI) analysis showed that that substrates act as electrophiles while the active zirconaaziridine behaves as a nucleophile. Furthermore, the distortion/interaction analysis unveiled the role of the distortion and interaction energies in controlling the regioselectivity and diastereoselectivity when different alkene substrates are used. These results provide an in-depth analysis on how the substrate type influences the product selectivity. © 2020 American Chemical Society. All rights reserved.

Authors
Fang R.1 , Zhou L. 2 , Kirillov A.M. 3, 4 , Yang L. 2
Journal
Organic Letters
Language
English
Status
Published
Link
External link
DOI
10.1021/ACS.ORGLETT.0C04119
Year
2021
Organizations
  • 1 Key Laboratory of Chemical Additives for China National Light Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an, 710021, China
  • 2 College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China
  • 3 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon, 1049-001, Portugal
  • 4 Research Institute of Chemistry, Peoples' Friendship University of Russia, RUDN University, Miklukho-Maklaya st., Moscow, 117198, Russian Federation
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