Highly stereoselective addition of Grignard reagents to C- cyclopropylnitrone via the bisected s-trans conformation. An efficient synthesis of PEDC, a potent NMDA receptor antagonist having a cyclopropane structure

Article abstract of DOI:10.1016/S0040-4039(00)00823-6

An efficient synthesis of PEDC (1), a potent NMDA receptor antagonist of a cyclopropane structure, was achieved. The highly stereoselective addition reaction of MeMgBr to C-cyclopropylnitrone 2, via its bisected s-trans conformation which can be predicted from the stereo-electronic effects, was developed as the key step. The s-trans conformation predominant in C- cyclopropynitrone 2 was suggested by NOE experiments. (C) 2000 Elsevier Science Ltd.