84466-42-2Relevant academic research and scientific papers
Biocatalytic asymmetric ring-opening of dihydroisoxazoles: a cyanide-free route to complementary enantiomers of β-hydroxy nitriles from olefins
Asano, Yasuhisa,Zheng, Daijun
supporting information, p. 4930 - 4936 (2020/08/25)
By combination of the cyanide-free synthesis of chiral nitriles and the Kemp elimination reaction catalyzed by aldoxime dehydratases, we herein report a new application of aldoxime dehydratase in the asymmetric ring-opening of 5-sub-4,5-dihydroisoxazoles
RhI-catalyzed aldol-type reaction of organonitriles under mild conditions
Goto, Akihiro,Endo, Kohei,Ukai, Yu,Irle, Stephan,Saito, Susumu
, p. 2212 - 2214 (2008/12/22)
An aldol-type reaction of organonitriles with aldehydes was catalyzed by a RhI(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components. The Royal Societ
Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: Lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles
Kamal, Ahmed,Khanna,Ramu
, p. 2039 - 2051 (2007/10/03)
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.
AN ALDOL-TYPE REACTION OF ACETONITRILES USING DIALKYLBORYL TRIFLATE
Hamana, Hiroshi,Sugasawa, Tsutomu
, p. 1401 - 1404 (2007/10/02)
Acetonitriles and benzaldehydes react in the presence of dialkyl boryl triflate and diisopropylethylamine in dichloromethane to give the corresponding aldol-type products in good yields under mild conditions.
