195388-55-7

Upstream product

• 195388-54-6 (R)-4-tert-butyl(4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yloxy)diphenylsilane 
• 1217683-02-7 C₂₂H₂₆Cl₂OSi 
• 1026451-65-9 tert-Butyl-((R)-3,4-dibromo-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-diphenyl-silane 
• 195388-53-5 (R)-4-bromo-1-tert-butyldiphenylsiloxy-1,2-dihydro-naphthalene 
• 195388-52-4 (R)-1-tert-butyldiphenylsiloxy-1,2-dihydro-naphthalene 
• 123849-23-0 (R)-(+)-1-hydroxy-1,2-dihydronaphthalene 

Downstream Products

• 167026-40-6 (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 79617-96-2 Sertraline 
• 87857-41-8 norsertraline 
• 195388-56-8 (1S,4S)-1-azido-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalene 
• 124379-29-9 (4S)-4-(3,4-dichlorophenyl)-1-tetralone 

Relevant academic research and scientific papers

Efficient enantioselective syntheses of sertraline, 2-epicatalponol and catalponol from tetralin-1,4-dione

Tetralin-1,4-dione, the stable tautomer of dihydroxynaphthalene, was reduced with catecholborane in the presence of 3,3-diphenyl-1-butyltetrahydro- 3H-pyrrolo[1,2-c][1,3,2]oxazaborole as catalyst to give enantiomerically highly enriched 4-hydroxy1-tetralone (99% ee) in an efficient one-pot procedure. The R-enantiomer provided a rapid access to sertraline while the S-enantiomer was converted into 2-epicatalponol and catalponol. A more selective enantioselective route to the antithermitic catalponol made use of the planar chiral tricarbonylchromium complex of hydroxytetralone. Its precursor chromium(tricarbonyl)[η6-(1-4,4a,8a)-tetralin-5,8dione] was obtained via direct complexation of 1,4-dihydroxynaphthalene using chromium(tricarbonyl)tris(ammonia) and boron trifluoride etherate as source of the chromium(tricarbonyl) fragment. Enolate prenylation was best carried out in the presence of a tetraamine ligand. Complete inversion of the stereogenic center bearing the prenyl group of the initially obtained tetralone complex was achieved via enolate formation followed by protonation.

Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline

Asymmetric reductive ring opening of oxabenzonorbornadiene provides dihydronaphthalenols in high ee and good yield. Functionality present in this system can be used to elaborate the core towards a number of targets. As an illustration, a concise stereoselective synthesis of the important antidepressant sertraline is described.