154807-85-9

Upstream product

• 154807-78-0 Ethyl 2-methyl-5-(4-methoxyphenyl)-2(E)-pentenoate 
• 154807-80-4 5-(4-Methoxyphenyl)-2-methyl-2(E)-penten-1-ol 
• 154807-81-5 1-Bromo-5-(4-methoxyphenyl)-2-methyl-2-pentene 
• 57707-91-2 (1S,2R,5S)-8-(+)-phenylmenthol 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 20401-88-1 3-(4-methoxyphenyl)propional 
• 609-14-3 2-acetylpropanoic acid ethyl ester 

Downstream Products

• 154807-86-0 (1R,4aR,10aS)-6-Methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Relevant academic research and scientific papers

Asymmetric Induction in Mn(III)-Based Oxidative Free-Radical Cyclizations of Phenylmenthyl Acetoacetates and 2,5-Dimethylpyrrolidine Acetoacetamides

Mn(III)-based oxidative free-radical cyclization of phenylmenthyl ester 1e afforded 90percent of 13 with 86percent de.Cyclization of 31b provided 56percent of (+)-podocarpic acid precursor 32e with 82percent de.The direction of de was opposite in these two cases.Oxidative cyclization of α-methyl β-keto ester 44b gave a 1:1.6 mixture of 46b and 47b while α-propyl β-keto ester 44d produced a >10:1 mixture of 46d and 47d indicating that the extent and direction of de is dependent on the size of the α-substituent.The reaction proceeds through transition states 12 and 56 with large α-substituents and through transition states 19 and 57 with small α-substituents.The de depends on the double-bond substitution pattern as shown by the decreased de with 37b and 37d, and selectivity in the 5-exo cyclization of 64b, 65b, 70b, and 71b is low.