265096-49-9

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 286-20-4 cyclohexane-1,2-epoxide 
• 286-20-4 cyclohexene oxide 
• 4513-77-3 2-cyanocyclohexanone 
• 75-77-4 chloro-trimethyl-silane 
• 30683-77-3 cis-2-hydroxycyclohexanecarbonitrile 

Downstream Products

• 125356-61-8 (1S,2R)-trans-2-hydroxycyclohexanecarbonitrile 

Relevant academic research and scientific papers

Enantiotopic Discrimination by Coordination-Desymmetrized meso-Ligands

The first examples of enantiopure catalysts that are chiral merely due to coordination of different metal ions at enantiotopic positions of an achiral meso-ligand are reported. These catalysts exhibit a pseudo-Cs symmetry and are able to catalyze reactions demanding simultaneous involvement of two catalytic sites. The latter was demonstrated by application in the asymmetric ring-opening of meso-epoxides.

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.

Asymmetric ring opening of epoxides with cyanides catalysed by chiral binuclear titanium complexes

A series of Schiff bases obtained from salicylaldehydes and 3,3′-diformyl-BINOL were synthesized. The complexes of these Schiff bases with Ti(IV) were active for the asymmetric ring opening of epoxides with TMSCN. A mixture of unpurified ligands was found

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.

Exceptionally active yttrium-salen complexes for the catalyzed ring opening of epoxides by TMSCN and TMSN3

(Chemical Equation Presented) Halide or alkoxide free yttrium-salen complexes are excellent catalysts for the ring opening of epoxides mediated by TMSCN and TMSN3. Substrate to catalyst ratios up to 10000 have been realized in these potentially

Polymer-bound pyridine-bis(oxazoline). Preparation through click chemistry and evaluation in asymmetric catalysis

A pyridine-bis(oxazoline) ligand was efficiently immobilized by copper(I)-catalyzed azidealkyne cycloaddition onto a polystyrene resin. The so obtained click-pybox resin la was associated with various metal salts (YbCl 3, LuCl3, CuOTf) and the resulting resin-bound catalysts were explored in ring-opening of cyclohexene oxide, silylcyanation of benzaldehyde and alkynylation of imines. These new polymer-supported catalysts exhibit good to excellent performances in terms of catalytic activity, enantioselectivity and recyclability.

(1R,2S)-4-(2-Cyano-cyclohexyl-oxy)-2-trifluoromethyl-benzonitrile, a potent androgen receptor antagonist for stimulating hair growth and reducing sebum production

Synthesis, pharmacology, and pharmacokinetic profiles of (1R, 2S)-4-(2-cyano-cyclohexyl-oxy)-2-trifluoromethyl-benzonitrile are reported. This compound demonstrated remarkable potency for stimulating hair growth in a male C3H mouse model as well as reduci

Chiral Ti(IV) complexes of hexadentate Schiff bases as precatalysts for the asymmetric addition of TMSCN to aldehydes and the ring opening of cyclohexene oxide

Chiral dinuclear titanium(IV) complexes (generated in situ from hexadentate Schiff bases and titanium tetra-isopropoxide) have been found to be more effective catalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes and the ring openin

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

Search for chiral catalysts through ligand diversity: Substrate-specific catalysts and ligand screening on solid phase

An efficient strategy in the search for chiral catalysts is ligand optimization on solid support. This diversity approach provides unique opportunities for the identification of substrate-specific catalysts and leads to the discovery of ligands with unusu