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.
Stereoselective synthesis of 3-amino-4-substituted-2-azetidinones via [2+2] cycloadditions of tricarbonyl(eta(6)arene)chromium(0)complexed imines / P. Del Buttero, G. Molteni, A. Papagni. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 14:24(2003), pp. 3949-3953. [10.1016/j.tetasy.2003.09.046]
Stereoselective synthesis of 3-amino-4-substituted-2-azetidinones via [2+2] cycloadditions of tricarbonyl(eta(6)arene)chromium(0)complexed imines
G. Molteni;
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 reserved.
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