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

Article Article scientifique Article Polycyclic Pyrazolidines by Tandem Diazomalonate Dipolar Cycloadditions and CpRu‐Catalyzed Carbene Additions eng 2024-05-10 2024-05-10 author Montagnon Claire 0009-0002-4019-2302 University of Geneva Organic Chemistry Department SWITZERLAND 928838 author Bultel Joël Ruben University of Geneva Organic Chemistry Department SWITZERLAND 678249 author Besnard Céline University of Geneva Laboratory of Crystallography SWITZERLAND 682138 Administration de la section de chimie (CHIAD) author Guenee Laure University of Geneva Laboratory of Crystallography SWITZERLAND 115015 Département de chimie minérale et analytique (CHIAM) author Lacour Jérôme 0000-0001-6247-8059 University of Geneva Department of Organic Chemistry Quai Ernest Ansermet 30 CH-1211 Geneva 4 SWITZERLAND 99165 Département de chimie organique (CHIOR) e202401522 10.1002/chem.202401522 38726887 0947-6539 https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202401522 <p>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%).</p> Carbenes Cycloaddition Diazo compounds Ruthenium Ylides Dewey 540 Swiss National Science Foundation Superstable Cations and Reactive ylides for Synthesis, Catalysis and (Bio)Optical Applications 184843 CH Projects Swiss National Science Foundation Superstable Chiral Cations and Reactive Ylides for Synthesis, Catalysis and Optical Applications 207539 CH Projects 36 Département de chimie organique 141 false 760 Groupe Lacour 1412 Groupe Laboratoire de Cristallographie Chemistry 4204f4c7-6214-4173-930a-85390671fa79 Article (Accepted version) Public Chemistry_A_European_J_-_2024_-_Mon.pdf 1682071 application/pdf Restricted 2025-05-11 e2fbd2754daa74b1e3013962d358a17997e4d62f4e91a346133ad5423ccffb6e 33cc1777-59e2-4df4-b2f6-1c5f30777b65 Article (Published version) Public Chemistry A European J - 2024 - Mon1.pdf 5800265 application/pdf CC BY-4.0 932720bab019fb1570bf0f9b74376b4f9f56c3c710dcc34aad2aa6a70932260d Vignette Public SSC December_abstract_JL.jpg 68549 image/png openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Title	Published in	Year	Views	Downloads

Polycyclic Pyrazolidines by Tandem Diazomalonate Dipolar Cycloadditions and CpRu‐Catalyzed Carbene Additions	Chemistry	2024	147	127
Nitrogen ylide formation and subsequent reactions via Cp-Ruthenium catalyzed diazo decomposition		2019	1,039	0

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Bultel, Joël Ruben