Zirconium-Catalyzed Hydroalumination of C=O Bonds: Site-Selective De-O-acetylation of Peracetylated Compounds and Mechanistic Insights
Thibaut Courant, Marine Gavel, Romain M. Q. Renard, Vincent Gandon, Antoine Y. P. Joosten and Thomas Lecourt*
*Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000 Rouen, France,
Email: thomas.lecourt
insa-rouen.fr
T. Courant, M. Gavel, R. M. Q. Renard, V. Gandon, A. Y. P. Joosten, T. Lecourt, J. Org. Chem., 2021, 86, 9280-9288.
DOI: 10.1021/acs.joc.1c00060
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Abstract
An unprecedented hydroalumination of C=O bonds catalyzed by zirconocene dichloride enables a site-selective deprotection of peracetylated functional substrates. A mixed metal hydride, with 1:1 zirconium/aluminum stoichiometry, is the reductive species.
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Computed Hydride Transfer with a 1:1 Zr/Al Cluster (kcal/mol)
Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides
M. Gavel, T. Courant, A. Y. P. Joosten, T. Lecourt, Org. Lett., 2019, 21, 1948-1952.
Key Words
deacetylation, DIBAL-H, Schwartz's Reagent
ID: J42-Y2021
