Polycyclic Pyrazolidines by Tandem Diazomalonate Dipolar Cycloadditions and CpRu‐Catalyzed Carbene Additions

Abstract: Thanks to the ability of diazo derivatives to react either as 1,3‐dipoles and as carbenes after dinitrogen extrusion, combinations of oxa or aza benzonorbornadienes and diazomalonates afford polycyclic pyrazolidines via a three‐step sequence of (i) a highly diastereoselective [3+2]‐cycloaddition, (ii) a CpRu‐catalyzed carbene addition, and (iii) a second dipolar cycloaddition. Of importance, step (II) represents a unique access to novel bench‐stable N,N‐cyclic azomethine imines, which behave as effective 1,3‐dipoles in combination with electron‐poor dipolarophiles. Each step proceeds efficiently and the 3‐step process can be performed in one‐pot to yield a polycyclic pyrazolidine in excellent overall yield (90 %).

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Polycyclic Pyrazolidines by Tandem Diazomalonate Dipolar Cycloadditions and CpRu‐Catalyzed Carbene Additions ; day:11 ; month:07 ; year:2024 ; extent:8 ; Chemistry - a European journal ; (11.07.2024) (gesamt 8)

Contributors, Places and Time

• Creator: Montagnon, Claire ; Bultel, Joël R. ; Besnard, Céline ; Guénée, Laure ; Lacour, Jérôme

Further information

• DOI: 10.1002/chem.202401522
• URN: urn:nbn:de:101:1-2407121418240.943516338488
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 14.08.2025, 11:01 AM CEST