Lyutin Ivan, Krivovicheva Vasilisa, Kantin Grigory, Dar'in Dmitry
Institute of Chemistry, Saint Petersburg State University, 26 Universitetskiy pr., Peterhof, Saint Petersburg 198504, Russian Federation.
Saint Petersburg Research Institute of Phthisiopulmonology, 2-4 Ligovsky pr., Saint Petersburg 191036, Russian Federation.
Beilstein J Org Chem. 2024 Aug 5;20:1894-1899. doi: 10.3762/bjoc.20.164. eCollection 2024.
In this work, we report an efficient approach to 2-oxoazetidine-3-carboxylic acid derivatives based on a thermally promoted Wolff rearrangement of diazotetramic acids in the presence of nucleophiles. The method allows easy variation of the substituent in the exocyclic acyl group by introducing different -, -, and -nucleophilic reagents into the reaction. The reaction of chiral diazotetramic acids leads exclusively to -diastereomeric β-lactams. The use of variously substituted diazotetramic acids, including spirocyclic derivatives, as well as a wide range of nucleophiles provides access to a structural diversity of medically relevant 2-oxoazetidine-3-carboxylic acid amides and esters.
在本工作中，我们报道了一种基于重氮四酰胺在亲核试剂存在下热促进的沃尔夫重排反应来制备2-氧代氮杂环丁烷-3-羧酸衍生物的有效方法。该方法通过向反应中引入不同的亲核试剂，可轻松改变环外酰基中的取代基。手性重氮四酰胺的反应仅生成非对映异构的β-内酰胺。使用各种取代的重氮四酰胺，包括螺环衍生物，以及多种亲核试剂，能够得到结构多样的具有医学相关性的2-氧代氮杂环丁烷-3-羧酸酰胺和酯。
