Advances in Deallylation
- 1 January 2021
- journal article
- review article
- Published by Shanghai Institute of Organic Chemistry in Chinese Journal of Organic Chemistry
- Vol. 41 (4), 1337-1358
- https://doi.org/10.6023/cjoc202009031
Abstract
Allyl groups, as a kind of universal protective groups in organic synthesis, are easily introduced, and stable under acidic, basic and reductive conditions. Moreover, the deallylation may occur efficiently and selectively under mild conditions. Therefore, functional group protection with allyl moiety plays a significant role in organic synthesis, especially in the synthesis of natural products and pharmaceutical industry. In recent decades, various methods of deallylation have been developed. Herein, the comprehensive development on the deallylation reaction with base and reductant, oxidation and free radical, Lewis-acid, iodine, transition metals, and electrochemical methods is reviewed.Keywords
This publication has 59 references indexed in Scilit:
- Highly practical iron-catalyzed C–O cleavage reactionsCatalysis Science & Technology, 2013
- Light-Triggered Ruthenium-Catalyzed Allylcarbamate Cleavage in Biological EnvironmentsOrganometallics, 2012
- Facile and Selective Deallylations of Esters under ‘Aqueous’ Free-Radical ConditionsSynlett, 2008
- Simple and Highly Efficient Method for the Deprotection of Allyl Ethers Using Dimethylsulfoxide–Sodium IodideSynthetic Communications, 2007
- Catalytic Removal of N-Allyloxycarbonyl Groups Using the [CpRu(IV)(π-C3H5)(2-quinolinecarboxylato)]PF6 Complex. A New Efficient Deprotecting Method in Peptide SynthesisThe Journal of Organic Chemistry, 2006
- [CpRu(IV)(π‐C3H5)(2‐quinolinecarboxylato)]PF6 Complex: A Robust Catalyst for the Cleavage and Formation of Allyl EthersAdvanced Synthesis & Catalysis, 2006
- Facile Deallylation Protocols for the Preparation of N-Unsubstituted Triazoles and TetrazolesThe Journal of Organic Chemistry, 2005
- Thiyl Radical-Mediated Cleavage of Allylic C−N Bonds: Scope, Limitations, and Theoretical Support to the MechanismJournal of the American Chemical Society, 2004
- Ruthenium‐Catalyzed Chemoselective N‐Allyl Cleavage: Novel Grubbs Carbene Mediated Deprotection of Allylic AminesChemistry – A European Journal, 2003
- Palladium-catalysed exchange of allylic groups of ethers and esters with active-hydrogen compoundsJournal of the Chemical Society D: Chemical Communications, 1970