title: Step-economical access to valuable Weinreb amide 2,5-disubstituted pyrrolidines by a sequential one-pot two-directional cross-metathesis/cyclizing aza-Michael process.
abstract: Double cross-metathesis of 1,5-hexadiene with a variety of electron-deficient alkenes including the reluctant Weinreb acrylamide has been successfully accomplished. It was found that the process is quite general, and microwave irradiation effectively accelerates cross-coupling metathesis. This promotes a very versatile and high yielding methodology for the synthesis of symmetric Michael acceptors, which can be transformed into 2,5-disubstituted pyrrolidines through a sequential one-pot two-directional cross-metathesis/ring-closing double aza-Michael process.
authors: Univ. Paris-Sud, Equipe de Chimie des Substances Naturelles, UMR CNRS 8076 BioCIS, 5 rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry, France.
authors: Hamza
authors: H
authors: Boufroura
authors: Marc
authors: M
authors: Mauduit
authors: Emmanuelle
authors: E
authors: Drège
authors: Delphine
authors: D
authors: Joseph
mesh_terms: D000178:Acrylamides / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D003500:Cyclization; D008872:Microwaves; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000178:Acrylamides; D000475:Alkenes; D003432:Cross-Linking Reagents; D011759:Pyrrolidines