A total synthesis of (1R, 5R)-3-phenylmethyl-4-thia-2,6-diazabicyclo [3.2.0]hept-2-en-7-one, a useful intermediate for the preparation of penem and cepham derivatives

Authors
Cainelli, G Giacomini, D Galletti, P
Citation
G. Cainelli et al., A total synthesis of (1R, 5R)-3-phenylmethyl-4-thia-2,6-diazabicyclo [3.2.0]hept-2-en-7-one, a useful intermediate for the preparation of penem and cepham derivatives, SYNTHESIS-S, (2), 2000, pp. 289-294
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
2
Year of publication
2000
Pages
289 - 294
Database
ISI
SICI code
0039-7881(200002):2<289:ATSO(5>2.0.ZU;2-L
Abstract
The preparation of the thiazoline (1R,SR)-3-phenylmethyl-4-thia-2,6-diazabi cyclo [3.2.0]hept-2-en-7-one (1) is presented. This compound, which has bee n extensively used as an intermediate for the synthesis of penems and cepha ms, has been obtained starting from a C-4 unsubstituted azetidinone by mean s of facile processes while chirality has been obtained through enzymatic r esolution.