Ni-H-Catalyzed Isomerization-Induced Cleavage of Allyl Ethers

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization: P. M. Kathe, A. Berkefeld, I. Fleischer

Synlett 2021, 32, DOI: 10.1055/s-0040-1706683


The concept of orthogonality, namely the selective removal of a protecting group through differential reactivity and stability in the presence of other protecting groups, is at the heart of organic synthesis. This is particularly important for the protection of hydroxy groups, owing to their ubiquitous nature. The allyl group is a very interesting option for protecting hydroxy groups, but there is a limited number of options in terms of chemoselective removal of O-allyl groups in the presence of other chemical functions. Recently, Professor Andreas Berkefeld and Dr. Ivana Fleischer from Eberhard Karls University Tübingen (Germany) reported a novel approach for achieving the orthogonal and mild deprotection of O-allyl to hydroxy groups.

Dr. Fleischer said: “The selective deprotection of O-allyl groups was achieved via an isomerization/hydrolysis sequence by combining a nickel hydride precatalyst and a Brønsted acid.”

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