A stereoselective synthesis of N-phenylsulfonyl substituted spiro-β- lactams obtained from the N-(phenylmethylene)benzenesulfonamide and the ketene valence tautomer of the bicyclic mesoionic compounds derived from 4- hydroxy substituted N-acyl-L-prolines in the presence of acetic anhydride as the dehydrating agent is presented. The reaction of (2S,4R)-4-acetyloxy or benzoyloxy-N-acyl-proline with the above imine afforded a mixture of two diastereoisomeric spiro-β-lactams with complete stereoselectivity for the spiro carbon.
Stereoselective synthesis of N-phenylsulfonyl substituted spiro-beta-lactams / P. Dalla Croce, C. La Rosa. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 10:6(1999), pp. 1193-1199. [10.1016/S0957-4166(99)00096-8]
Stereoselective synthesis of N-phenylsulfonyl substituted spiro-beta-lactams
P. Dalla CrocePrimo
;C. La RosaUltimo
1999
Abstract
A stereoselective synthesis of N-phenylsulfonyl substituted spiro-β- lactams obtained from the N-(phenylmethylene)benzenesulfonamide and the ketene valence tautomer of the bicyclic mesoionic compounds derived from 4- hydroxy substituted N-acyl-L-prolines in the presence of acetic anhydride as the dehydrating agent is presented. The reaction of (2S,4R)-4-acetyloxy or benzoyloxy-N-acyl-proline with the above imine afforded a mixture of two diastereoisomeric spiro-β-lactams with complete stereoselectivity for the spiro carbon.Pubblicazioni consigliate
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