Electrochemical generation of chiral oxazolidin-2-ones anions: a new procedure for the highly diastereoselective conjugate addition to nitroalkenes

A mild and efficient electrochemical alternative to classical base-catalyze d conjugate addition of nitrogen nucleophiles is reported here. The cleavag e of the carbamic N . H bond of Evans' chiral auxiliaries can be very effic iently performed by electrolysis under galvanostatic control and the result ing naked anions used for highly, diastereoselective conjugate addition to nitroalkenes. The degree of stereoselectivity was shown to depend on the st eric hindrance of the group at the ring C(4) of the starting oxazolidin-2-o ne. (C) 2001 Elsevier Science Ltd. All rights reserved.