147189-95-5

Upstream product

• 118528-87-3 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid 
• 50597-19-8 3-(3,4-dichlorobenzoyl)-propionic acid 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 147189-94-4 (1R)-(3,4-Dichlorophenyl)-1,4-butanediol 

Downstream Products

• 147255-16-1 (4R)-4-(3,4-dichlorophenyl)-4-phenylbutanoic acid 
• 124379-29-9 (4S)-4-(3,4-dichlorophenyl)-1-tetralone 
• 155748-61-1 (4R)-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone 
• 147189-96-6 (2S)-(3,4-Dichlorophenyl)tetrahydrofuran 
• 147189-97-7 (1R)-(3,4-Dichlorophenyl)-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenylbutane 
• 147189-98-8 (1R)-(3,4-Dichlorophenyl)-1-phenylbutane-4-ol 
• 147213-96-5 (1R)-(3,4-Dichlorophenyl)-α-<3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>propyl>methanesulfonate benzenemethanol 

Relevant academic research and scientific papers

Synthesis of 4(S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone by SN2 cuprate displacement of an activated chiral benzylic alcohol

Two routes for the preparation of 4(S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone are reported. The most efficient route generates a chiral benzylic alcohol by catalytic asymmetric oxazaborolidine reduction of a γ-ketoester that is subsequently activated and displaced in an SN2 manner with a higher order cuprate. Intramolecular Friedel-Crafts cyclization of the resulting t-butylester affords the title compound.