195392-61-1Relevant articles and documents
Functionalization of a β-lactam ring via nucleophilic displacement of a 4-vinyloxy substituent
Kaluza, Zbigniew
, p. 1025 - 1026 (2007/10/03)
A vinyloxy group at C-4 of an azetidin-2-one can be easily displaced by nucleophiles in the presence of a Lewis acid catalyst.
Stereocontrolled synthesis of 1-oxacepham from 4-vinyloxyazetidin-2-one, a new building block
Kaluza, Zbigniew,Lysek, Robert
, p. 2553 - 2560 (2007/10/03)
A new methodology for 1-oxacepham synthesis is described. Readily available 4-vinyloxyazetidin-2-one 2 is shown to be a useful building block for β-lactam synthesis. N-Alkylation of 2 is followed by oxidation of the vinyloxy group to give 4-acyloxy-N-substituted azetidin-2-ones suitable for nucleophilic displacement at the C-4 carbon atom. The ring closure reaction offers high stereoselectivity.