Work

Dynamic Kinetic Asymmetric [3 + 2] Annulation Reactions of Aminocyclopropanes

Year: 2014

Type: article

Abstract: We report the first example of a dynamic kinetic asymmetric [3 + 2] annulation reaction of aminocyclopropanes with both enol ethers and aldehydes. Using a Cu catalyst and a commercially available bisoxazoline ligand, cyclopentyl- and tetrahydrofurylamines were obtained in 69-99% yield and up to a 98:2 enantiomeric ratio using the same reaction conditions. The method gives access to important enantio-enriched nitrogen building blocks for the synthesis of bioactive compounds.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja5024578

Authors: Florian de Nanteuil, Eloisa Serrano, Daniele Perrotta, Jerome Waser

Institution: École Polytechnique Fédérale de Lausanne

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Roche, Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Awards: Cyclization Reactions: New Access towards Active Substances against Cancer and Neurologic Diseases, Annulation Reactions: Stereoselective Access to Nitrogen-Rich Building Blocks for the Synthesis of Bioactive Compounds