ChemInform Abstract: CaF2-Catalyzed SN2-type Chlorodehydroxylation of Chiral Secondary Alcohols with Thionyl Chloride: A Practical and Convenient Approach for the Preparation of Optically Active Chloroalkanes.

ChemInform ◽  
2013 ◽  
Vol 44 (32) ◽  
pp. no-no
Author(s):  
Junjie Zhang ◽  
Huanxia Wang ◽  
Yun Ma ◽  
Youming Wang ◽  
Zhenghong Zhou ◽  
...  
Keyword(s):  
Thionyl Chloride ◽  
Optically Active ◽  
Secondary Alcohols ◽  
Convenient Approach

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.

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