Ferrier-Petasis rearrangement of 4-(vinyloxy)azetidin-2-ones: an entry to carbapenams and carbacephams.
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.
Kozioł
Anna
A
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Grzeszczyk
Barbara
B
Kozioł
Andrzej
A
Staszewska-Krajewska
Olga
O
Furman
Bartłomiej
B
Chmielewski
Marek
M
D001384:Azetidines / Q000737:chemistry*; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
C116379:2-azetidinone; D001384:Azetidines; D015780:Carbapenems; D002511:Cephalosporins; C026739:carbacephems