654065-58-4

Upstream product

• 709668-01-9 (2S,5R)-5-Methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexanone O-methyl-oxime 
• 654065-56-2 (2S,5R,E)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexan-1-one oxime 
• 205057-17-6 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone 
• 108-86-1 bromobenzene 
• 97371-54-5 (-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon 

Relevant academic research and scientific papers

Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines

The electrochemical generation of menthylamines from the corresponding menthone oximes equipped with an additional substituent in position 8 is described. Due to 1,3-diaxial interactions a pronounced diastereoselectivity for the menthylamines is found.

Enantiodifferentiating [2+2] photocycloaddition of cyclohexenone carboxylic acid with ethylene using 8-phenylmenthyl amine as a chiral template

Enantiodifferentiating [2+2] photocycloaddition of cyclohexenone carboxylic acid with the smallest olefin, ethylene, was accomplished using 8-phenylmenthyl amine as a chiral template. Particularly, we succeeded in enhancing the enantiomeric excess (ee) value by selective excitation of a chiral substrate-template supramolecular complex.

ELECTROCHEMICAL PRODUCTION OF STERICALLY HINDERED AMINES

The present invention relates to a process for preparing an amine, which comprises the step cathodic reduction of a corresponding oxime derivative of the general formula (I) where R is C1-6-alkyl or C2-6-alkenyl which is optionally substituted by one or more substituents selected independently from the group consisting of phenyl, O—C1-6-alkyl, NH—C1-6-alkyl, N(C1-6-alkyl)2, OH and NH2;R1 is H; C1-6-alkyl or C(O)—C1-6-alkyl and A is a 5-, 6- or 7-membered hydrocarbon ring which is saturated or has a double bond and in which at least one CH2 group may, if appropriate, be replaced by —O—, —S— —NH—, —N═ or —N(C1-6-alkyl)- and which may optionally be substituted by one or more further substituents selected independently from the group consisting of phenyl, C1-6-alkyl, O—C1-6-alkyl, NH—C1-6-alkyl, N(C1-6-alkyl)2, OH and NH2; wherein, based on the ring carbon bearing the substituent R, the oxime derivative has an excess of the R or S form of at least 10%.

Stereoselective synthesis of activated cyclopropanes with an α-pyridinium acetamide bearing an 8-phenylmenthyl group as the chiral auxiliary

The reaction between an α-pyridinium acetamide bearing an 8-phenylmenthyl group as the chiral auxiliary and β-substituted methylidenemalononitriles gave rise to trans-cyclopropanes with diastereomeric ratios of up to 98:2. For most of the reactions, the absolute stereochemistry of the major product was found to be opposite of that of the major products of the reaction of the corresponding ester series, which also utilized the 8-phenylmenthyl group.

Synthesis and Characterization of Enantiomerically Pure Menthylamines and Their Isocyanates

A synthetic protocol for optically pure (-)-menthylamine, (-)-8-methylmenthylamine, and the novel (-)-8-phenylmenthylamine is presented including a detailed characterization of these compounds and their isocyanates.