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 Croce
Primo
;
C. La Rosa
Ultimo
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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/190251
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