The pent-4-enoyl group: a novel amine-protecting group that is readily cleaved under mild conditions

…, C Roberts, B Fraser-Reid

Index: Madsen, Robert; Roberts, Carmichael; Fraser-Reid, Bert Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 7920 - 7926

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Citation Number: 75

Abstract

Primary and secondary amines are readily protected as N-pent-kenoyl 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,