96101-62-1

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 108-94-1 cyclohexanone 
• 286-20-4 cyclohexane-1,2-epoxide 
• 286-20-4 cyclohexene oxide 
• 110-83-8 cyclohexene 
• 75-77-4 chloro-trimethyl-silane 
• 63301-31-5 trans-2-cyanocyclohexanol 

Downstream Products

• 63301-31-5 trans-2-cyanocyclohexanol 
• 125356-62-9 (1R,2S)-2-hydroxycyclohexane-1-carbonitrile 

Relevant academic research and scientific papers

Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes.

The asymmetric ring opening of meso epoxides with TMSCN is catalyzed by (pybox)YbCl3 complexes, yielding the beta-trimethylsilyloxy nitrile ring-opened products with good enantioselectivities (83-92% ee). The reaction exhibits a second-order kinetic depen

Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles

A stereoselective bioreduction of 2-oxocycloalkanecarbonitriles was concurrently coupled to a whole cell-catalyzed nitrile hydrolysis in one-pot. The first step, mediated by ketoreductases, involved a dynamic reductive kinetic resolution, which led to 2-hydroxycycloalkanenitriles in very high enantio- and diastereomeric ratios. Then, the simultaneous exposure to nitrile hydratase and amidase from whole cells of Rhodococcus rhodochrous provided the corresponding 2-hydroxycycloalkanecarboxylic acids with excellent overall yield and optical purity for the all-enzymatic cascade.

Scope and limitations of one-pot multistep reactions with heterogeneous catalysts: The case of alkene epoxidation coupled to epoxide ring-opening

The combination of two reactions in one-pot multistep system requires the compatibility not only between the catalysts of both reactions, but also between all the reaction components and conditions. In the case of the coupling of alkene epoxidation and epoxide ring opening, it has been possible to synthesize cyanohydrin and azidohydrin derivatives through a simple process that involves a one-pot multistep process by using a mixture of two heterogeneous catalysts, a silica-grafted Ti catalyst and ytterbium chloride, whose efficiency depends on the reactivity of the starting alkene. In addition, in some cases the mixture of catalysts can be recovered and reused in several one-pot multistep cycles. However, this system is not possible with electron-deficient alkenes, as the basic catalyst required for epoxidation has shown to be incompatible with the ring-opening process.

Efficient ring opening of epoxides with trimethylsilyl azide and cyanide catalyzed by erbium(III) triflate

Epoxides can be opened under neutral conditions with TMSN3 and TMSCN in the presence of catalytic amounts of Lewis acid, affording the corresponding ring-opened compounds in high yields.

Asymmetric meso-epoxide ring-opening with trimethylsilyl cyanide promoted by chiral binuclear complexes of titanium. Dichotomy of C-C versus C-N bond formation

In the presence of chiral catalysts derived from the same chiral hexadentate ligand and aluminium, zinc or titanium ions, the reaction between cyclohexene oxide and trimethylsilyl cyanide can be controlled to give predominantly either the nitrile (up to 99% ee) or the isonitrile product (up to 94% ee). The metal ion, ligand stereochemistry and base concentration all play a role in determining the product ratio.

A chemoenzymatic synthesis of an androgen receptor antagonist

A new scalable enzymatic resolution approach to both enantiomers of trans-2-hydroxycyclohexanecarbonitrile (9 and 11) was developed. Treatment of the racemic mixture (4) with succinic anhydride in the presence of Novozym 435 led to selective acylation of one enantiomer to the corresponding hemisuccinate, which was separated from the unreacted enantiomer by a simple basic extraction. This procedure produced the desired enantiomer in high ee, while obviating the need for chromatography or expensive catalysts and ligands. The application of this protocol to the large-scale synthesis of an androgen receptor antagonist (1) is described.

Tetraaryl-1,3-dioxolane-4,5-dimethanols as catalysts for the addition of trimethylsilyl cyanide to benzaldehyde and the oxirane ring

The synthesis of 1,2-, 1,3-, and 1,4-phenylene-bis[(4R,5R)-4,5- di(hydroxydiphenylmethyl)-1,3-dioxolane]s (ortho-, meta-, and para-bis-(R,R)-TADDOLs) and bis[4-{[(4R, 5R)-4,5-di(hydroxydiphenylmethyl)]-1,3- dioxolan-2-yl}phenyl]methane was carried out. The possibilities of the use of these compounds as catalysts for the C-C bond formation in the addition of Me3SiCN to benzaldehyde and the oxirane ring opening in cyclohexene oxide by Me3SiCN were investigated. The catalytic activity of different bis-(R, R)-TADDOLs in this series depends on their structure.

Ring opening of oxiranes catalyzed by Mn-Salen immobilized mesoporous materials

Mn-Salen Immobilized mesoporous materials were found to be efficient solid catalysts for the nucleophilic ring opening of oxiranes with TMSN3, TMSCN and aniline.

Etnwicklung von chiralen Katalysatoren durch kombinatorische Ligandenvariation - Ti-katalysierte enantioselective Addition von TMSCN an meso-Epoxide

Keywords: Asymmetrische Katalyse; Cyanhydrine; Epoxide; Kombinatorische Chemie; Peptide