STEREOCONTROLLED SYNTHESIS OF 1-OXACEPHAM FROM 4-VINYLOXYAZETIDIN-2-ONE, A NEW BUILDING-BLOCK

Authors
KALUZA Z LYSEK R
Citation
Z. Kaluza et R. Lysek, STEREOCONTROLLED SYNTHESIS OF 1-OXACEPHAM FROM 4-VINYLOXYAZETIDIN-2-ONE, A NEW BUILDING-BLOCK, Tetrahedron : asymmetry, 8(15), 1997, pp. 2553-2560
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
15
Year of publication
1997
Pages
2553 - 2560
Database
ISI
SICI code
0957-4166(1997)8:15<2553:SSO1F4>2.0.ZU;2-Y
Abstract
A new methodology for 1-oxacepham synthesis is described. Readily avai lable 4-vinyloxyazetidin-2-one 2 is shown to be a useful building bloc k for beta-lactam synthesis. N-Alkylation of 2 is followed by oxidatio n of the vinyloxy group to give 4-acyloxy-N-substituted azetidin-2-one s suitable for nucleophilic displacement at the C-4 carbon atom. The r ing closure reaction offers high stereoselectivity. (C) 1997 Elsevier Science Ltd.