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

Garcia, Alvaro Enriquez
Ouizem, Souad
Published in Advanced Synthesis and Catalysis. 2010, vol. 352, no. 13, p. 2306 - 2314
Abstract 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.
Keywords Arene complexesAsymmetric reductionChromium tricarbonylPrenylationTautomerism
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Other version: http://doi.wiley.com/10.1002/adsc.201000384
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GARCIA, Alvaro Enriquez et al. Efficient Enantioselective Syntheses of Sertraline, 2-Epicatalponol and Catalponol from Tetralin-1,4-dione. In: Advanced Synthesis and Catalysis, 2010, vol. 352, n° 13, p. 2306 - 2314. https://archive-ouverte.unige.ch/unige:11952

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Deposited on : 2010-09-30

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