Journal
TETRAHEDRON LETTERS
Volume 52, Issue 17, Pages 2140-2143Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.11.064
Keywords
Asymmetric catalysis; Asymmetric hydroxylation; Rare earth metal; Tetrasubstituted stereogenic centers; Amide-based ligand
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Funding
- MEXT
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A catalytic asymmetric hydroxylation of N-nonsubstituted alpha-alkoxycarbonyl amides is described. A new effective catalyst comprising Pr((OPr)-Pr-i)(3) and a fluoro-substituted amide-based ligand was identified using oxaziridine as the oxidizing reagent. The catalyst components were in dynamic equilibrium in the reaction mixture, which assembled to form the associated transition state through metal coordination and hydrogen bonding. (C) 2010 Elsevier Ltd. All rights reserved.
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