Traceless Isoprenylation of Aldehydes via
<i>N</i>
‐Boc‐
<i>N</i>
‐(1,1‐dimethylallyl)hydrazones
作者:Desirée Heerdegen、Julia Junker、Sebastian Dittrich、Peter Mayer、Franz Bracher
DOI:10.1002/ejoc.202000382
日期:2020.6.30
1‐dimethylallyl)hydrazones was developed utilising Thomson's traceless bond construction. This type of [3,3]‐sigmatropic rearrangement is catalysed by the Bronsted acid triflimide and liberates only gaseous by‐products. The required N‐Boc‐N‐allylhydrazine precursor is available in three steps starting from a known diazene using biocatalytic aldol addition and Tebbe olefination as key steps. Allylhydrazones are prepared
利用 Thomson 的无痕键结构开发了一种从非共轭 N-Boc-N-(1,1-二甲基烯丙基)腙开始的短异戊二烯化方案。这种类型的 [3,3]-σ 重排由布朗斯台德酸三氟甲磺酸酯催化并仅释放气态副产物。所需的 N-Boc-N-烯丙基肼前体可通过三个步骤从已知的二氮烯开始,使用生物催化醛醇加成和 Tebbe 烯化作为关键步骤。烯丙基腙是通过与合适的醛缩合制备的。分析了 [3,3]-sigmatropic 重排的范围和局限性。