title: Recent contributions from the asymmetric aza-Michael reaction to alkaloids total synthesis.
abstract: This review focuses on recent applications of the aza-Michael reaction in alkaloids total synthesis with a special emphasis on stereoselectivity. The report highlights achievements and challenges over the past five years and describes stereoselective intra- and inter-molecular conjugate addition of nitrogen-containing nucleophiles, including tandem and cascade processes. Total asymmetric syntheses of natural scaffolds, such as pyrrolidine, piperidine and "izidine" families, are depicted. Multi-step syntheses of highly challenging natural products are further detailed, assessing the scope of the stereocontrolled aza-Michael reaction as a powerful tool in alkaloid chemistry.
authors.affiliation: Université Paris Sud, UMR CNRS 8076 BioCIS, LaBex LERMiT, Equipe de Chimie des Substances naturelles, 5, rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry Cedex, France.
authors.forename: Zacharias
authors.initials: Z
authors.lastname: Amara
authors.forename: Joachim
authors.initials: J
authors.lastname: Caron
authors.forename: Delphine
authors.initials: D
authors.lastname: Joseph
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000470:Alkaloids; D001688:Biological Products