HIGHLY ENANTIOSELECTIVE CONSTRUCTION OF THE KEY AZETIDIN-2-ONES FOR THE SYNTHESIS OF CARBAPENEM ANTIBIOTICS VIA INTRAMOLECULAR C-H INSERTION REACTIONS OF ALPHA-METHOXYCARBONYL-ALPHA-DIAZOACETAMIDES CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXYLATES

Authors
ANADA M WATANABE N HASHIMOTO S
Citation
M. Anada et al., HIGHLY ENANTIOSELECTIVE CONSTRUCTION OF THE KEY AZETIDIN-2-ONES FOR THE SYNTHESIS OF CARBAPENEM ANTIBIOTICS VIA INTRAMOLECULAR C-H INSERTION REACTIONS OF ALPHA-METHOXYCARBONYL-ALPHA-DIAZOACETAMIDES CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXYLATES, Chemical communications, (15), 1998, pp. 1517-1518
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
15
Year of publication
1998
Pages
1517 - 1518
Database
ISI
SICI code
1359-7345(1998):15<1517:HECOTK>2.0.ZU;2-N
Abstract
A highly enantioselective construction of 3-oxa-1-azabicyclo[4,2,0]oct anes (up to 96% ee) has been achieved by intramolecular C-H insertion of alpha-methoxycarbonyl-alpha-diazoacetamides catalysed by dirhodium( II) complexes incorporating N-phthaloyl-(S)-amino acids as chiral brid ging ligands, which provides a new, catalytic asymmetric route to key intermediates for carbapenem antibiotics.