title: Passerini Reactions on Biocatalytically Derived Chiral Azetidines.
abstract: The purpose of this study was to explore a series of Passerini reactions on a biocatalytically derived enantiopure azetidine-2-carboxyaldehyde in order to obtain, in a diastereoselective manner, polyfunctionalised derivatives having the potential to be cyclized to chiral bridged bicyclic nitrogen heterocycles. While diastereoselectivity was poor under classical Passerini conditions, a significant increase of diastereoselectivity (up to 76:24) was gained by the use of zinc bromide as promoter. The methodology has a broad scope and yields are always good.
authors: Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy. lisa.moni@unige.it.
authors: Lisa
authors: L
authors: Moni
authors: Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy. banfi@chimica.unige.it.
authors: Luca
authors: L
authors: Banfi
authors: Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy. andrea.basso@unige.it.
authors: Andrea
authors: A
authors: Basso
authors: Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy. 3342868@studenti.unige.it.
authors: Andrea
authors: A
authors: Bozzano
authors: Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy. martina.spallarossa@gmail.com.
authors: Martina
authors: M
authors: Spallarossa
authors: Leibniz-Institut für Pflanzenbiochemie, Weinberg 3, 06120 Halle (Saale), Germany. wessjohann@ipb-halle.de.
authors: Ludger
authors: L
authors: Wessjohann
authors: Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy. riva@chimica.unige.it.
authors: Renata
authors: R
authors: Riva
mesh_terms: D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001384:Azetidines
keywords: azetidines; biocatalysis; isocyanides; multicomponent reactions