155095-22-0

Upstream product

• 75-36-5 acetyl chloride 
• 155095-10-6 (4R,7S)-3-phenyl-4-methyl-7-isopropyl-4,5,6,7-tetrahydro-1H-indazole 
• 155095-12-8 (3R,6S)-2-Benzoyl-3-methyl-6-isopropylcyclohexanone 
• 98-88-4 benzoyl chloride 
• 10458-14-7 (2R,5S)-menthone 

Downstream Products

• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 16197-93-6 (S)-1-phenylethyl acetate 
• 16197-92-5 (R)-1-phenethyl acetate 
• 1565-74-8 (R)-1-phenyl-1-propanol 
• 613-87-6 (S)-1-phenyl-1-propanol 
• 2114-29-6 (R)-1-phenylpropyl acetate 
• 2114-29-6 (S)-1-phenylpropyl acetate 
• 3391-10-4 (S)-1-(4-Chlorophenyl)ethanol 
• 3391-10-4 (R)-1-(4-chlorophenyl)ethan-1-ol 
• 19759-43-4 (S)-1-(4-chlorophenyl)ethyl acetate 
• 19759-43-4 (R)-1-(4-chlorophenyl)ethyl acetate 
• 7287-82-3 (S)-1-(2-Methylphenyl)ethanol 
• 42070-90-6 (R)-1-(2-methylphenyl)ethanol 

Relevant academic research and scientific papers

Resolution of secondary alcohols using 2-acyl-3-phenyl-l-menthopyrazoles as enantioselective acylating agents

The chelation of AlCl3 with N-acylpyrazoles leads to structural fixation of the acyl moiety and an acceleration in the rate of acylation of secondary alcohols. The chiral environment of the fixed acyl moiety of 2-acyl-3-phenyl-l-menthopyrazole 2 causes diastereofacial selectivity in the reaction with secondary alcohols, and thus 2 behaves as an enantioselective acylating agent. By the use of 2.4 molar equivalents of racemic 1-phenylethanol 3a, 2-acetyl-3-phenyl-l-menthopyrazole 2a afforded (S)-1-phenylethyl acetate (S)-4aa enantioselectively and unreacted 3a was recovered with (R)-configuration. Furthermore, the inverse configurational preferences were observed to give (R)-4aa and (S)-3a by the addition of strongly basic amines, which sometimes behaved as catalysts for enolate formation from 2 and AlCl3. These dramatic changes in stereoselective preference should be useful properties of 2-acyl-3-phenyl-l-menthopyrazole 2 as an enantioselective acylating agent.

Asymmetric reaction of diethylzinc with aldehydes catalyzed by l-menthopyrazole derivatives

N-Hydroxyalkyl-1-menthopyrazoles acted as a chiral catalyst for the diethylzinc (1) addition to aromatic aldehydes, and 1-aryl-1-propanols were afforded enantioselectively. These reactions were carried out optimally in toluene at 40°C in the presence of 3

Stereoselective N-acylation of a new chiral auxiliary compound; 3-phenyl-l-menthopyrazole

As a new chiral auxiliary compound having a pyrazole ring system, the synthetic utility of (4R,7S)-3-phenyl-4-methyl-7-isopropyl-4,5,6,7-tetrahydroindazole (3-phenyl-l-menthopyrazole), which was prepared from l-menthone, was discussed.