66984-23-4

Upstream product

• 1713-33-3 1,2-epoxy-1-methylcyclohexane 
• 75-77-4 chloro-trimethyl-silane 
• 7677-24-9 trimethylsilyl cyanide 
• 151-50-8 potassium cyanide 
• 646-20-8 pimelonitrile 
• 5670-51-9 (+/-)-1-methyl-2-oxo-1-cyclohexanecarbonitrile 
• 5775-23-5 1-phenylcyclohexene oxide 
• 15595-71-8 2-aminocyclohex-1-enecarbonitrile 
• 591-49-1 1-methylcyclohex-1-ene 
• 4513-77-3 2-cyanocyclohexanone 

Downstream Products

• 406909-97-5 (1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile 

Relevant academic research and scientific papers

Synthesis and Enzymatic Kinetic Resolution of α,α -Disubstituted Cyclic Hydroxy Nitriles

Herein, we describe the diastereoselective synthesis of five- and six-membered α,α-disubstituted cyclic β-hydroxy nitriles and their resolution via enzymatic transesterification. By this method, all possible stereoisomers were obtained in enantiopure form and high yield.

Preparation of enantiopure ketones and alcohols containing a quaternary stereocenter through parallel kinetic resolution of β-keto nitriles

Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kineticresolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.

Easy Direct Stereo- and Regioselective Formation of β-Hydroxy Nitriles by Reaction of 1,2-Epoxides with Potassium Cyanide in the Presence of Metal Salts

A simple efficient, anti stereoselective, and highly regioselective method for the synthesis of β-hydroxy nitriles by the direct opening of 1,2-epoxides with KCN in acetonitrile, in the presence of metal salts, is described.This new method appears to be competitive with the other methods previously reported. Key words: β-hydroxy nitriles; epoxide opening reactions; regioselectivity; catalysts.

Reaction of Cyanotrimethylsilane with Oxiranes. Effect of Catalysts or Mediators on Regioselectivity and Ambident Character

Reaction of cyanotrimethylsilane with oxiranes under the catalytic action of Lewis acids Pd(CN)2, SnCl2, or Me3Ga affords 2-trimethylsiloxy isocyanides by regio- and stereoselective attack of isocyanide on the more substituted carbon.The reaction mediated by aluminium alkoxides gives predominantly 3-trimethylsiloxy nitriles by the selective attack of cyanide on the less substituted carbon.