Asymmetrie aerobic oxidation of α-hydroxy acid derivatives by C 4-symmetric, vanadate-centered, tetrakisvanadyl(V) clusters derived from N-salicylidene-α-aminocarboxylates

Chien Tien Chen, Sampada Bettigeri, Shiue Shien Weng, Vijay D. Pawar, Ya Hui Lin, Cheng Yuan Liu, Way Zen Lee

研究成果: 雜誌貢獻文章

47 引文 斯高帕斯(Scopus)

摘要

(Chemical Equation Presented) A series of chiral vanadyl(V) methoxides bearing 3-t-butyl-5-substituted N-salicylene-L-valinate and L-t-leucinate as chiral auxiliaries has been prepared. In all cases except the 3,5-di-t-butyl analogue, they exist as monomers both in solution and in the single crystal state. In the case of the 3,5-di-t-butyl analogue, the architectural nature of the vanadyl(V) complex highly depends on the base used during the complex formation event. A pentanuclear C4-symmetric complex was formed when potassium salts were employed instead of the corresponding sodium salts. A central vanadate(V) unit serves to grip four identical chiral monomelic vanadyl(V) units together, by which a potassium ion sits on top of the four flanking units through carbonyl coordinations and serves to hold the whole cluster by cooperation with the central vanadate(V) unit. In comparison with the corresponding monomelic vanadyl(V) methoxide complex, the cluster complex was utilized to facilitate the asymmetric aerobic oxidations of various racemic α-hydroxyesters, -amides, and -thioesters with excellent selectivity factors (krel 40 to >500).

原文英語
頁(從 - 到)8175-8185
頁數11
期刊Journal of Organic Chemistry
72
發行號22
DOIs
出版狀態已發佈 - 2007 十月 26

ASJC Scopus subject areas

  • Organic Chemistry

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