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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 (free Supporting Information)


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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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Key Words

Acetates, Schwartz's Reagent


ID: J54-Y2019