S(N)2 reaction of 2-substituted 3-piperidinol mesylate with retention of configuration: application to the asymmetric synthesis of (2R,3S)-CP-99,994
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Starting from protected (S)-3-hydroxyglutarimide 2a, the asymmetric synthesis of (2R,3S)-CP-99,994 8 was achieved. The crucial steps were a neighboring group participation leading to pyrrolidino-aziridinium intermediate 25 and the subsequent regioselective ring-opening reaction. In the case where neighboring group participation was not involved, only the eliminated product 15 was obtained. (c) 2006 Published by Elsevier Ltd.