A mild and efficient electrochemical alternative to classical base-catalyzed conjugate addition of nitrogen nucleophiles is reported here. The cleavage of the carbamic N . H bond of Evans' chiral auxiliaries can be very efficiently performed by electrolysis under galvanostatic control and the resulting naked anions used for highly, diastereoselective conjugate addition to nitroalkenes. The degree of stereoselectivity was shown to depend on the steric hindrance of the group at the ring C(4) of the starting oxazolidin-2-one. (C) 2001 Elsevier Science Ltd. All rights reserved.
Electrochemical generation of chiral oxazolidin-2-ones anions: a new procedure for the highly diastereoselective conjugate addition to nitroalkenes / Feroci, Marta; Inesi, Achille; Laura, Palombi; Leucio, Rossi. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 12:16(2001), pp. 2331-2335. [10.1016/s0957-4166(01)00385-8]
Electrochemical generation of chiral oxazolidin-2-ones anions: a new procedure for the highly diastereoselective conjugate addition to nitroalkenes
FEROCI, Marta;INESI, ACHILLE;
2001
Abstract
A mild and efficient electrochemical alternative to classical base-catalyzed conjugate addition of nitrogen nucleophiles is reported here. The cleavage of the carbamic N . H bond of Evans' chiral auxiliaries can be very efficiently performed by electrolysis under galvanostatic control and the resulting naked anions used for highly, diastereoselective conjugate addition to nitroalkenes. The degree of stereoselectivity was shown to depend on the steric hindrance of the group at the ring C(4) of the starting oxazolidin-2-one. (C) 2001 Elsevier Science Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
