The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions

Article abstract of DOI:10.1021/jo00129a036

Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline.Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution.Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.