Asymmetric reactions. XX. Some factors influencing the course of asymmetric reduction by optically active alkoxy lithium aluminium hydrides

1967 ◽  
Vol 32 (11) ◽  
pp. 3897-3908 ◽  
Author(s):  
O. Červinka ◽  
O. Bělovský
Keyword(s):  
Asymmetric Reduction ◽  
Optically Active ◽  
Asymmetric Reactions ◽  
Lithium Aluminium ◽  
Factors Influencing

scholarly journals Synthesis of 2-Amino-apopinan-3-ol and Applications of Its Derivatives in Asymmetric Reduction of Ketones

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 63
Author(s):  
Anna Kmieciak ◽  
Marek P. Krzemiński
Keyword(s):  
Amino Alcohol ◽  
Asymmetric Reduction ◽  
Optically Active ◽  
Asymmetric Reactions ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Active Compounds ◽  
Reduction Methods ◽  
Optically Pure ◽  
Reduction Of Ketones

Monoterpenes are optically active compounds which occur in nature. This fact makes them interesting precursors for the synthesis of optically active ligands, which can be applied in various asymmetric reactions. In this work, we present the synthesis of optically pure 2-amino-apopinan-3-ol from (−)-α-pinene. The obtained amino alcohol was used as a precursor of oxazaborolidine, which was used as catalyst in the asymmetric reduction of aryl-alkyl ketones with borane. In the second part, we transformed 2-amino-apopinan-3-ol into PHOX ligand in a three-step reaction. The complex of ruthenium precursor with PHOX ligand was used as a catalyst in the asymmetric transfer hydrogenation of aryl-alkyl ketones. Alcohols with enantiomeric excesses of up to 97% were isolated using both reduction methods.

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%.

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