93085-88-2

Upstream product

• 99647-67-3 (+/-)-trans-2,2-dimethyl-3-phenylcyclopropanecarbonitrile 
• 50672-13-4 (+/-)-2,2-dimethyl-3c-phenyl-cyclopropane-r-carboxylic acid 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 99647-67-3 2,2-dimethyl-3-phenyl-cyclopropanecarbonitrile 

Downstream Products

• 50672-13-4 (±)-trans-2,2-dimethyl-3-phenylcyclopropanecarboxylic acid 
• 494846-57-0 (-)-trans-(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarboxylic acid 
• 494846-26-3 (+)-trans-(1R,3R)-2,2-dimethyl-3-phenylcyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Cyclopropyl aryl amide derivatives and uses thereof

Compounds of the formula: wherein Ar1, Ar2, R1 and R2 are as defined herein. Also provided are pharmaceutical compositions, methods of using, and methods of preparing the subject compounds.

Synthesis of high enantiomeric purity gem-dihalocyclopropane derivatives from biotransformations of nitriles and amides

Enantioselective biotransformations of geminally dihalogenated cyclopropanecarbonitriles and amides are described. Both the reaction rate and enantioselectivity of the nitrile hydratase and amidase involved in Rhodococcus sp. AJ270 microbial cells are strongly governed by the nature of gem-disubstituents on the cyclopropane ring; the amidase generally exhibits steric dependence on the substituents while both the steric and electronic factors of the substituents may affect the action of the nitrile hydratase. The match of steric bulkiness of the substituents at 2- with that at 3-positions on the cyclopropane ring benefits the efficient and highly enantioselective reaction. Coupled with facile chemical transformations, biocatalytic transformations of nitrile and amide supply an effective synthesis of optically active 2,2-disubstitued-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms.

Nitrile biotransformation for highly enantioselective synthesis of 3-substituted 2,2-dimethylcyclopropanecarboxylic acids and amides

Biotransformations of differently configured 2,2-dimethyl-3-substitued-cyclopropanecarbonitriles were studied using a nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 whole-cell catalyst under very mild conditions. Although all of the cis-3-aryl-2,2-dimethylcyclopropanecarbonitriles appeared inert toward the biocatalyst, a number of racemic trans-isomers efficiently underwent a highly enantioselective hydrolysis to produce (+)-(1R,3R)-3-aryl-2,2-dimethylcyclopropanecarboxylic acids and (-)-(1S,3S)-3-aryl-2,2-dimethylcyclopropanecarboxamides in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of 1R-enantioselective nitrile hydratase and amidase, with the later being a dominant factor. The influence of the substrates on both reaction efficiency and enantioselectivity was discussed in terms of steric and electronic effects. Coupled with chemical transformations, biotransformations of nitriles provided convenient syntheses of optically pure geminally dimethyl-substituted cyclopropanecarboxylic acids and amides, including chrysanthemic acids, in both enantiomeric forms.

Nitrile and Amide Biotransformations for Efficient Synthesis of Enantiopure gem-Dihalocyclopropane Derivatives

Catalyzed by Rhodococcus sp. AJ270 microbial cells, trans-2,2-dihalo-3- phenylcyclopropanecarbonitriles and -amides underwent enantioselective hydrolysis under very mild conditions. Both the efficiency and enantioselectivity of the nitrile hydratase and a