Silicon Lewis Acid Catalyzed [3+2] Cycloaddition Reactions of Hydrazones/Cyclopentadiene: Mild Access to Pyrazolidine Derivatives

Journal article


Publication Details

Author(s): Zamfir A, Schenker S, Bauer W, Clark T, Tsogoeva S
Journal: European Journal of Organic Chemistry
Publisher: Wiley-VCH Verlag
Publication year: 2011
Journal issue: 20-21
Pages range: 3706-3709
ISSN: 1434-193X


Abstract


A first and fairly mild metal-free catalytic route was developed for the [3+2] cycloadditions of different N-acylhydrazones to cyclopentadiene, providing the synthetically and biologically important five-membered cyclic compounds pyrazolidines. The reaction was successfully conducted in high yields (up to 99%) with high diastereoselectivities (up to 98: 2 dr) by using catalytic amounts of TMSOTf (trimethylsilyl triflate) as a readily available Lewis acidic catalyst. The experimental findings were supported by DFT calculations of the reaction mechanism. The theoretical and experimental diastereomeric excess values show good agreement, rendering the computations an efficient tool for predicting the selectivities in these and related reactions.



FAU Authors / FAU Editors

Bauer, Walter apl. Prof. Dr.
Lehrstuhl für Organische Chemie II
Clark, Timothy apl. Prof. Dr.
Computer-Chemie-Centrum
Schenker, Sebastian Dr. rer. nat.
Naturwissenschaftliche Fakultät
Tsogoeva, Svetlana Prof. Dr.
Professur für Organische Chemie


How to cite

APA:
Zamfir, A., Schenker, S., Bauer, W., Clark, T., & Tsogoeva, S. (2011). Silicon Lewis Acid Catalyzed [3+2] Cycloaddition Reactions of Hydrazones/Cyclopentadiene: Mild Access to Pyrazolidine Derivatives. European Journal of Organic Chemistry, 20-21, 3706-3709. https://dx.doi.org/10.1002/ejoc.201100206

MLA:
Zamfir, Alexandru, et al. "Silicon Lewis Acid Catalyzed [3+2] Cycloaddition Reactions of Hydrazones/Cyclopentadiene: Mild Access to Pyrazolidine Derivatives." European Journal of Organic Chemistry 20-21 (2011): 3706-3709.

BibTeX: 

Last updated on 2019-20-07 at 07:22