Asymmetric reduction of p-alkylacetophenones

1986 ◽  
Vol 51 (3) ◽  
pp. 684-686 ◽  
Author(s):  
Otakar Červinka ◽  
Anna Fábryová ◽  
Ivana Brožová ◽  
Miroslav Holík
Keyword(s):  
Asymmetric Reduction ◽  
Optically Active ◽  
Lithium Aluminium Hydride ◽  
Lithium Aluminium

Asymmetric reduction of p-alkylacetophenones Ia-VIIa with lithium aluminium hydride in the presence of (-)-quinine affords optically active alcohols Ib-VIIb of the (R)-(+) configuration in optical yields of about 50%.

Preparation of secondary alcohols of high optical purity

1986 ◽  
Vol 51 (2) ◽  
pp. 401-403 ◽  
Author(s):  
Otakar Červinka ◽  
Anna Fábryová ◽  
Irina Sablukova
Keyword(s):  
Nmr Spectroscopy ◽  
Optical Purity ◽  
Optically Active ◽  
Secondary Alcohols ◽  
Lithium Aluminium Hydride ◽  
Enantioselective Reduction ◽  
H Nmr ◽  
Lithium Aluminium ◽  
High Optical Purity ◽  
Optically Pure

Partially resolved enantiomers of optically active alcohols I-V, obtained by enantioselective reduction of the corresponding ketones with lithium aluminium hydride in the presence of (-)-quinine, were converted into crystalline 3,5-dinitrobenzoates or phenylcarbamates. The esters of the nearly optically pure enantiomers were separated by crystallization from the generally more soluble esters of the racemates. Optical purity of the hydrolytically liberated alcohols was determined by 1H NMR spectroscopy in the presence of chiral shifting agents.

Studies of the optically active compounds of Anacardiaceae Exudates. IV. The structures of the rearrangement products from the long chain alicyclic ketoalocohol of Tigaso oil in Alkali

1958 ◽  
Vol 11 (4) ◽  
pp. 538
Author(s):  
JA Lamberton
Keyword(s):  
Methyl Ether ◽  
Active Compound ◽  
Monomethyl Ether ◽  
Optically Active ◽  
Side Chain ◽  
Lithium Aluminium Hydride ◽  
Active Compounds ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Long Chain

The structure IIIa previously proposed for the β-diketone with an unsaturated side chain, obtained by the action of alkali on the optically active compound of Tigaso oil, is confirmed by the formation of methyl stearyl ketone and resorcinol monomethyl ether in the pyrolysis of the methyl ether (IV). An anomalous lithium aluminium hydride reduction of the methyl ether (IV) and other reactions are discussed. Unsuccessful attempts have been made to synthesize the tribasic acid resulting from sodium hypobromite oxidation of the β-diketone (IIIb).

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