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標題: Asymmetric zinc-Reformatsky reaction of Evans chiral imide with acetophenones and its application to the stereoselective synthesis of triazole antifungal agents
作者: Yu, L.T.
Ho, M.T.
Chang, C.Y.
Yang, T.K.
關鍵字: ketones;condensation;aldehydes;additions;esters;nickel
Project: Tetrahedron-Asymmetry
期刊/報告no:: Tetrahedron-Asymmetry, Volume 18, Issue 8, Page(s) 949-962.
The Ni(acac)(2) catalytic ZnEt2-mediated asymmetric Reformatsky-type reaction of Evans chiral imide with various acetophenones was studied. The chiral imido zinc enolate, which was formed through the metal-halogen exchange reaction of chiral alpha-bromopropionyl-2-oxazolidinones 2 with diethyl zinc under the catalysis of Ni(acac)(2), performed the asymmetric zinc-Reformatsky reaction with activated alpha-haloacetophenones 3 to give the chiral beta-hydroxyamide 4 in good yields and high ratios of syn-(2R,3R)-isomers (up to > 97%). This new asymmetric synthesis technology affords a practical method to synthesize the versatile chiral building block 5 for triazole antifungal agents, such as Voriconazole, Ravuconazole, TAK-187, and RO-0094815. (c) 2007 Published by Elsevier Ltd.
ISSN: 0957-4166
DOI: 10.1016/j.tetasy.2007.03.015
Appears in Collections:期刊論文

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