title: Ferrier-Petasis rearrangement of 4-(vinyloxy)azetidin-2-ones: an entry to carbapenams and carbacephams.
abstract: Trimethylsilyl triflate promotes Ferrier-Petasis rearrangement of 4-(vinyloxy)-, 4-(propenyloxy)-, and 4-(isopropenyloxy)azetidin-2-ones to corresponding 4-(carbonylmethyl)azetidin-2-ones. The latter compounds may serve as attractive intermediates in the synthesis of carbapenem antibiotics. To illustrate the potential of this reaction, selected rearrangement products have been transformed into carbapenams.
authors.affiliation: Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Kozioł
authors.forename: Barbara
authors.initials: B
authors.lastname: Grzeszczyk
authors.forename: Andrzej
authors.initials: A
authors.lastname: Kozioł
authors.forename: Olga
authors.initials: O
authors.lastname: Staszewska-Krajewska
authors.forename: Bartłomiej
authors.initials: B
authors.lastname: Furman
authors.forename: Marek
authors.initials: M
authors.lastname: Chmielewski
mesh_terms: D001384:Azetidines / Q000737:chemistry*; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: C116379:2-azetidinone; D001384:Azetidines; D015780:Carbapenems; D002511:Cephalosporins; C026739:carbacephems