Scientific article

Efficient Enantioselective Syntheses of Sertraline, 2-Epicatalponol and Catalponol from Tetralin-1,4-dione

Published inAdvanced synthesis & catalysis, vol. 352, no. 13, p. 2306-2314
Publication date2010

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-hydroxy-1-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-5,8-dione] 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.

  • Arene complexes
  • Asymmetric reduction
  • Chromium tricarbonyl
  • Prenylation
  • Tautomerism
Citation (ISO format)
GARCIA, Alvaro Enriquez et al. Efficient Enantioselective Syntheses of Sertraline, 2-Epicatalponol and Catalponol from Tetralin-1,4-dione. In: Advanced synthesis & catalysis, 2010, vol. 352, n° 13, p. 2306–2314. doi: 10.1002/adsc.201000384
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Article (Published version)
ISSN of the journal1615-4150

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