- Asymmetric Hydrogenation of β-Aryloxy/Alkoxy Cinnamic Nitriles and Esters
-
A highly efficient and enantioselective hydrogenation of β-aryloxy/alkoxy cinnamic nitriles and esters under mild conditions has been realized by using a rhodium catalyst with a chiral f-spiroPhos ligand. The method provides efficient access to the asymme
- Kong, Duanyang,Li, Meina,Wang, Rui,Zi, Guofu,Hou, Guohua
-
supporting information
p. 4916 - 4919
(2016/10/18)
-
- Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: Lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles
-
A facile preparation of (±)-3-hydroxy-3-phenylpropanenitrile has been carried out by ring-opening of styrene oxide with NaCN in aqueous ethanol. Subsequent kinetic resolution of this material via lipase-mediated transesterification gave the S-alcohol and R-acetate in excellent yields and high enantioselectivities, particularly with lipase PS-C 'Amano' II. The effect of solvents and immobilization of the lipase has also been investigated. It is interesting to note that the use of immobilized lipase for this transesterification process in hydrophobic solvents (diisopropyl ether, toluene and hexane) enhanced the reaction rate drastically and gave optimal yields with high enantioselectivity (>99%). Moreover, enantiopure 3-hydroxy-3-phenylpropanenitrile products have been converted via enantioconvergent routes into the (R)- and (S)-enantiomers of the important anti-depressants fluoxetine, tomoxetine, nisoxetine and norfluoxetine.
- Kamal, Ahmed,Khanna,Ramu
-
p. 2039 - 2051
(2007/10/03)
-
- Chemoenzymatic synthesis of the non-tricyclic antidepressants Fluoxetine, Tomoxetine and Nisoxetine
-
3-Chloro-1-phenylpropan-1-ol and the corresponding butanoate, 3-chloro-1-phenyl-1-propyl butanoate, were kinetically resolved using lipase B from Candida antarctica catalysis by transesterification and hydrolysis respectively. The resulting chiral building blocks (S)- and (R)-3-chloro-1-phenylpropanol were converted into both enantiomers of the antidepressant drugs, Fluoxetine, Tomoxetine and Nisoxetine. The Royal Society of Chemistry 2000.
- Liu, Hui-Ling,Hoff, Bard Helge,Anthonsen, Thorleif
-
p. 1767 - 1769
(2007/10/03)
-
- An efficient route to enantiomerically pure antidepressants: Tomoxetine, nisoxetine and fluoxetine
-
Both enantiomers (R)- and (S)-3-chloro-1-phenyl-1-propanol can be obtained conveniently by an efficient enzymatic resolution process. They can be converted via enantioconvergent routes into all enantiomers of the important antidepressants (R)- and (S)-Tomoxetine, Fluoxetine and Nisoxetine.
- Schneider,Goergens
-
p. 525 - 528
(2007/10/02)
-