Department of Chemistry, Tunghai University, No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung City, 40704 Taiwan, Republic of China.
Org Lett. 2020 Mar 20;22(6):2391-2395. doi: 10.1021/acs.orglett.0c00586. Epub 2020 Mar 9.
A simple protocol for the protection of amines was realized through a base-catalyzed one-pot reaction of dimedone, β-nitroalkene, and amine. Employing this strategy, a variety of amines/amino acids were protected in excellent yields. These acid/base stable protected amines can be deprotected by either ethylene diamine or hydrazine hydrate under mild conditions. The practical application of this orthogonal protecting group was demonstrated by the synthesis of cyclic peptide melanotan II via SPPS.
通过二亚甲基酮、β-硝基烯烃和胺的碱催化一锅反应，实现了一种简单的保护胺的方案。采用该策略，各种胺/氨基酸以优异的收率得到保护。这些酸/碱稳定的保护胺可以在温和条件下通过乙二胺或水合肼脱保护。该正交保护基的实际应用通过 SPPS 合成环肽黑色素 II 得到了证明。
