198561-32-9

Upstream product

• 62455-70-3 3-cyclohexyl-3-oxopropanenitrile 
• 876-27-7 4-chlorophenyl acetate 
• 126678-67-9 rac-3-cyclohexyl-3-hydroxypropionitrile 
• 75-05-8 acetonitrile 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1161512-46-4 5-cyclohexyl-2-isoxazoline 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 3483-39-4 Cyclohexyloxirane 
• 143-33-9 sodium cyanide 
• 198561-25-0 2-cyano-1-cyclohexylethyl acetate 

Relevant academic research and scientific papers

Biocatalytic strategy toward asymmetric β-hydroxy nitriles and γ-amino alcohols

A library of 20 bakers' yeast reductases, that are overexpressed in Escherichia coli, were screened against a variety of β-keto nitriles. Enzymes from the aldose reductase and the short chain dehydrogenase family displayed activity toward these substrates. All of the seven substrates were reduced with high enantioselectivities and in some cases both antipodes could be synthesized in high ees. These whole-cell reactions afforded gram quantities of asymmetric compounds that could ultimately lead to scaleable and simple synthesis to new drug analogs of serotonin reuptake inhibitors and β-adrenergic blocking agents.

Engineering a Carbonyl Reductase for Scalable Preparation of (S)-3-Cyclopentyl-3-hydroxypropanenitrile, the Key Building Block of Ruxolitinib

(S)-3-Cyclopentyl-3-hydroxypropanenitrile is the key precursor for the synthesis of ruxolitinib. The bioreduction of 3-cyclopentyl-3-ketopropanenitrile (1 a) offers an attractive method to access this important compound. A carbonyl reductase (PhADH) from

Iridium diamine catalyst for the asymmetric transfer hydrogenation of ketones

A simple and very efficient chiral aqua iridium(III) diamine complex leads to excellent enantioselectivities in the asymmetric transfer hydrogenation of various α-cyano and α-nitro ketones. The catalyst provides the ortho-substituted aromatic alcohols with especially high ee values. The diamine ligands can be used directly as chiral ligands; conversion into the corresponding sulfamide is not necessary.

Base-catalyzed isomerization of 2-isoxazolines enables a two-step enantioselective synthesis of β-hydroxynitriles from enals

The asymmetric synthesis of β-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of β-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of β-hydroxynitriles from α,β-unsaturated aldehydes in high enantiomeric purity.

Enantioselective ring opening of epoxides with cyanide catalysed by halohydrin dehalogenases: A new approach to non-racemic β-hydroxy nitriles

Halohydrin dehalogenases (HheA, HheB and HheC) were found to efficiently catalyse a carbon-carbon bond forming reaction between terminal aliphatic epoxides and cyanide, yielding β-hydroxy nitriles. With all three enzymes nucleophilic ring opening of epoxi

Cu(I)-catalyzed direct enantioselective cross aldol-type reaction of acetonitrile

(Chemical Equation Presented) Direct catalytic enantioselective cross aldol-type reaction of an acetate surrogate was developed using Cu alkoxide-chiral phosphine complexes as catalysts. Chemoselective activation and deprotonation of the donor substrate (

Method of manufacturing cyano compounds

A method of manufacturing a cyano compound by reacting a carbonyl compound with a nitrile compound having at least one α-hydrogen atom in the presence of a ligand and a metal compound of formula (III), [in-line-formulae]MX??(III) [/in-line-formulae] where

Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. A Route to Useful Precursors for γ-Amino Alcohols

An efficient kinetic resolution of racemic β-hydroxy nitriles 1 was performed via Candida antarctica lipase (N-435)-catalyzed transesterification. A variety of racemic alkyl, aryl, and aryloxymethyl substituted β-hydroxy nitriles was efficiently transformed to the corresponding enantiomerically pure acetates (ee > 99% and conversion = 50%) with E values from 40 to > 1000. The combination of the enzymatic kinetic resolution with a ruthenium-catalyzed alcohol racemization led to a dynamic kinetic resolution (ee's up to 99%, yields up to 85%).

Enantio- and chemoselective bioreduction of β-keto nitriles by the fungus Curvularia lunata

The use of methanol as cosolvent allows the chemoselective reduction of aromatic β-keto nitriles by the fungus Curvularia lunata CECT 2130, yielding the corresponding (S)-β-hydroxy nitriles in a highly enantioselective way. Copyright (C) 2000 Elsevier Science Ltd.

Thiacrown Ether Technology in Lipase-Catalyzed Reaction: Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomehtyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.