title: Solvent- and Catalyst-Free Synthesis of Nitrogen-Containing Bicycles through Hemiaminal Formation/Diastereoselective Hetero-Diels-Alder Reaction with Diazenes.
abstract: A solvent- and catalyst-free synthesis of nitrogen-containing bicyclic derivatives through a three-bond forming process is reported. Starting from dienals and readily available diazenes, the strategy involving the hemiaminal formation/hetero-Diels-Alder reaction affords the bicyclic products in a highly diastereoselective manner. This simple and green procedure has been applied to a selection of substrates, giving rise to 12 examples of nitrogen-containing bicyclic architectures. These products underwent various synthetic transformations. A sequence involving the cleavage of the hydrazine allowed the preparation of a hydantoin motif bearing an aminopropyl side chain, which is a structure found in natural products. A mechanism has also been suggested to explain the observed selectivities.
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, 45 Avenue des États-Unis, 78035 Versailles cedex France.
authors.forename: Laurence
authors.initials: L
authors.lastname: Crouillebois
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, 45 Avenue des États-Unis, 78035 Versailles cedex France.
authors.forename: Loïc
authors.initials: L
authors.lastname: Pantaine
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, 45 Avenue des États-Unis, 78035 Versailles cedex France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Marrot
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, 45 Avenue des États-Unis, 78035 Versailles cedex France.
authors.forename: Vincent
authors.initials: V
authors.lastname: Coeffard
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, 45 Avenue des États-Unis, 78035 Versailles cedex France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Moreau
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, 45 Avenue des États-Unis, 78035 Versailles cedex France.
authors.forename: Christine
authors.initials: C
authors.lastname: Greck
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D007094:Imides; C038867:diazene; D009584:Nitrogen