The stereoselective [2+2] cycloaddition reaction between the chiral tricarbonyl(eta(6)arene) chromium(0) complexed imines 1 and 6 and phthalimidoketene affords tricarbonyl (eta(6)arene)chromium(0) complexed 3-phthalimido-2-azetidinones 3, 7 and 8, both in racemic and enantiopure form. Decomplexation and the cleavage of the phthalimido group give 3-amino-4-substituted-2-azetidinones 5 and 10. Some insights into the stereochemical outcome of the [2+2] cycloaddition process are discussed. (C) 2003 Elsevier Ltd. All rights reserved
Del Buttero, P., Molteni, G., Papagni, A. (2003). Stereoselective synthesis of 3-amino-4-substituted-2-azetidinones via [2+2] cycloadditions of tricarbonyl(η6arene)chromium(0)complexed imines. TETRAHEDRON-ASYMMETRY, 14(24), 3949-3953 [10.1016/j.tetasy.2003.09.046].
Stereoselective synthesis of 3-amino-4-substituted-2-azetidinones via [2+2] cycloadditions of tricarbonyl(η6arene)chromium(0)complexed imines
PAPAGNI, ANTONIO
2003
Abstract
The stereoselective [2+2] cycloaddition reaction between the chiral tricarbonyl(eta(6)arene) chromium(0) complexed imines 1 and 6 and phthalimidoketene affords tricarbonyl (eta(6)arene)chromium(0) complexed 3-phthalimido-2-azetidinones 3, 7 and 8, both in racemic and enantiopure form. Decomplexation and the cleavage of the phthalimido group give 3-amino-4-substituted-2-azetidinones 5 and 10. Some insights into the stereochemical outcome of the [2+2] cycloaddition process are discussed. (C) 2003 Elsevier Ltd. All rights reservedI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.