2,2,6,6-Tetramethylpiperidin-1-yloxycarbonyl: A Protecting Group for Primary, Secondary, and Heterocyclic Amines
作者:Joseph R. Lizza、Maximilian Bremerich、Stephanie R. McCabe、Peter Wipf
DOI:10.1021/acs.orglett.8b02874
日期:2018.11.2
n-1-yloxycarbonyl (Tempoc) protecting group is readily introduced by the reaction of amines with a new acyl transfer reagent, 4-nitrophenyl (2,2,6,6-tetramethylpiperidin-1-yl) carbonate (NPTC). Tempoc has a reactivity profile that complements the commonly used t-butyloxycarbonyl (Boc) and benzyloxycarbonyl (Cbz) protecting groups. Deprotection can be achieved under mild reductive conditions with in
2,2,6,6-四甲基哌啶-1-基氧羰基(Tempoc)保护基很容易通过胺与新的酰基转移试剂4-硝基苯基(2,2,6,6-四甲基哌啶-1-基碳酸)(NPTC)。Tempoc具有与常用的叔丁氧羰基(Boc)和苄氧羰基(Cbz)保护基团互补的反应活性。可以在温和的还原条件下用原位生成的Cu(I)物种或通过在135°C下热裂解来实现脱保护。对Tempoc-吲哚脱保护的机理研究表明,在热条件下,离子和自由基的断裂途径结合在一起。