Catalytic asymmetric synthesis of chiral diol, bis[2-(1-hydroxyalkyl)-phenyl]ether, an asymmetric autocatalytic reaction

Chiral diols, bis[2-(1-hydroxyalkyl)phenyl]ethers, with very high e.e.'s are synthesized by catalytic enantioselective alkylation of bis(2-formylphenyl)ether. Zinc alkoxides of chiral diols were found to work as asymmetric autocatalysts in the reaction between bis(2-formylphenyl)ether and dialk...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 5; no. 5; pp. 789 - 792
Main Authors Soai, Kenso, Hayase, Tadakatsu, Shimada, Chieko, Isobe, Koichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.05.1994
Elsevier
Elsevier Science
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ALCOHOLS
BENZALDEHYDE
HIGHLY ENANTIOSELECTIVE ADDITION
DIETHYLZINC
COMPLEXES
DIALKYLZINC REAGENTS
ALDEHYDES
ACETALS
INDUCTION
AUTOINDUCTION
Aldehydoether
Benzenic compound
Hydroxyether
Autocatalysis
Asymmetric reaction
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Summary:Chiral diols, bis[2-(1-hydroxyalkyl)phenyl]ethers, with very high e.e.'s are synthesized by catalytic enantioselective alkylation of bis(2-formylphenyl)ether. Zinc alkoxides of chiral diols were found to work as asymmetric autocatalysts in the reaction between bis(2-formylphenyl)ether and dialkylzincs. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(00)86228-X