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Zirconium-Salan Catalyzed Enantioselective alpha-Hydroxylation of beta-Keto Esters

Title
Zirconium-Salan Catalyzed Enantioselective alpha-Hydroxylation of beta-Keto Esters
Authors
Chen, JieGu, HaiyangZhu, XueyingNam, WonwooWang, Bin
Ewha Authors
남원우
SCOPUS Author ID
남원우scopus
Issue Date
2020
Journal Title
ADVANCED SYNTHESIS & CATALYSIS
ISSN
1615-4150JCR Link

1615-4169JCR Link
Citation
ADVANCED SYNTHESIS & CATALYSIS vol. 362, no. 14, pp. 2976 - 2983
Keywords
Asymmetric catalysisHydroxylationIndoxacarbOxidationZirconium
Publisher
WILEY-V C H VERLAG GMBH
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
We report herein the development of enantioselective and scalable alpha-hydroxylation of 1-indanone-derived beta-keto esters by Zr(IV) complexes bearing readily availableC(2)-symmetric salan ligands and cumene hydroperoxide as an oxidant, affording synthetically valuable hydroxylation products in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee) under mild reaction conditions. In mechanistic studies, we have shown that (1) a Zr(IV)-salan complex was generated in situ as the active catalyst responsible for the chiral induction, (2) the transfer of the electrophilic fragment from cumene hydroperoxide to the Zr(IV)-bound enolate was accompanied by a heterolytic O-O bond cleavage, and (3) the formation of hydrogen bond between the amine hydrogen atom(s) of the salan ligand and the hydroxy group of cumene hydroperoxide was significant for stabilizing the stereocontrolled transition state and improving the enantioselectivity.
DOI
10.1002/adsc.202000290
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자연과학대학 > 화학·나노과학전공 > Journal papers
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