Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides

Marine Gavel, Thibaut Courant, Antoine Yvan Philippe Joosten, Thomas Lecourt*

*Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000 Rouen, France, Email: Thomas.Lecourtinsa-rouen.fr

M. Gavel, T. Courant, A. Y. P. Joosten, T. Lecourt, Org. Lett., 2019, 21, 1948-1952.

DOI: 10.1021/acs.orglett.8b03947

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Abstract

A combination of Cp₂ZrCl₂ and DIBAL-H promotes a regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds.

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Zirconium-Catalyzed Hydroalumination of C=O Bonds: Site-Selective De-O-acetylation of Peracetylated Compounds and Mechanistic Insights

T. Courant, M. Gavel, R. M. Q. Renard, V. Gandon, A. Y. P. Joosten, T. Lecourt, J. Org. Chem., 2021, 86, 9280-9288.

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Key Words

Acetates, Schwartz's Reagent

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ID: J54-Y2019