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Elsevier, Tetrahedron: Asymmetry, 23(17), p. 3265-3272

DOI: 10.1016/j.tetasy.2006.12.009

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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

Journal article published in 2006 by Liang-Xian Liu, 黄培强, Pei-Qiang Huang ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

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.