MONOCARBOXYLATES OF 3-METHYLIDENE-BETA-LACTAMS - SYNTHESIS AND UNUSUAL OXIDATIVE REARRANGEMENT INTO A SPIRO[AZETIDINE-3,3'-PYRROLIDINE] DERIVATIVE

Authors
JOHNER M RIHS G GURTLER S OTTO HH
Citation
M. Johner et al., MONOCARBOXYLATES OF 3-METHYLIDENE-BETA-LACTAMS - SYNTHESIS AND UNUSUAL OXIDATIVE REARRANGEMENT INTO A SPIRO[AZETIDINE-3,3'-PYRROLIDINE] DERIVATIVE, Helvetica Chimica Acta, 77(8), 1994, pp. 2147-2152
Citations number
12
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
77
Issue
8
Year of publication
1994
Pages
2147 - 2152
Database
ISI
SICI code
0018-019X(1994)77:8<2147:MO3-SA>2.0.ZU;2-1
Abstract
Reaction of the 3-silylated beta-lactams 1 with glycoxalates gives bis -lactam 3, but the same reaction in the presence of 1 equiv. of Me(3)S iCl leads to the formation of the disilylated adducts 5. The latter is desilylated by (Bu(4)N)F yielding the monocarboxylates 7 of 3-methyli dene-beta-lactams, which, with oxidizing agents, give the spiro compou nd 8. The structure of 8 is established by spectroscopic data and a cr ystal-structure analysis.