Journal
TETRAHEDRON
Volume 67, Issue 34, Pages 6221-6226Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.055
Keywords
Piperazinone; Asymmetric synthesis; Chiral auxiliary; Dynamic resolution; Nucleophilic substitution
Categories
Funding
- Korea Research Foundation [2009-0089650]
- Seoul RBD Program [WR090671]
- National Research Foundation of Korea [2009-0089650] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Dynamic resolution of alpha-halo esters derived from five chiral alcohols has been investigated in nucleophilic substitution with ethylenediamine nucleophiles. Stereoselective substitution of alpha-halo esters and following spontaneous cyclization provide a practical protocol for asymmetric syntheses of 3-substituted piperazin-2-ones up to 94:6 er. (C) 2011 Elsevier Ltd. All rights reserved.
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