Enantioselective Aerobic Oxidation of α-Hydroxy-Ketones Catalyzed by Oxidovanadium(V) Methoxides Bearing Chiral, N-Salicylidene-tert-butylglycinates

被引：57

作者：

Chen, Chien-Tien ^{[1
]}

Kao, Jun-Qi ^{[2
]}

Salunke, Santosh B. ^{[2
]}

Lin, Ya-Hui ^{[2
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan

[2] Natl Taiwan Normal Univ, Dept Chem, Taipei, Taiwan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 01期

关键词：

ENANTIOMER-DIFFERENTIATING OXIDATION; BENZOIN CONDENSATION; SECONDARY ALCOHOLS; KINETIC RESOLUTION; MOLECULAR-OXYGEN; KURASOIN-A; COMPLEXES; 2-NAPHTHOLS; INHIBITORS; AMINOCARBOXYLATES;

D O I：

10.1021/ol1024053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral oxidovanadium(V) methoxides prepared from 3,5-disubstituted-N-salicylidene-L-tert-butylglycines and vanadyl sulfate in air-saturated MeOH serve as highly enantioselective catalysts for asymmetric aerobic oxidations and kinetic resolution of alkyl, aryl, and heteroaryl alpha-hydroxyketones: with differed alpha-substituents at ambient temperature in toluene or TBME (tert-butyl methyl ether). The best scenarios involve the use of complexes which bear the tridendate templates derived from 3,5-diphenyl- or 3-o-biphenyl-5-nitro-salicyaldehyde. The kinetic resolution selectivities of the aerobic oxidation process are in the range of 12 to >1000 based on the selectivity factors (k(rel)).

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页码：26 / 29

页数：4

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