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

Article Article scientifique Article Efficient Enantioselective Syntheses of Sertraline, 2-Epicatalponol and Catalponol from Tetralin-1,4-dione eng 2010 author Garcia Alvaro Enriquez author Ouizem Souad author Cheng Xin 689848 author Romanens Patrick 22629 author Kundig Ernst Peter 26401 2306-2314 10.1002/adsc.201000384 1615-4150 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 Dewey 540 36 Département de chimie organique 141 false Advanced synthesis & catalysis 352 13 d4c00844-3288-4548-a514-f100078dd536 Article (Published version) Restricted 2306_ftp.pdf 286454 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Efficient Enantioselective Syntheses of Sertraline, 2-Epicatalponol and Catalponol from Tetralin-1,4-dione	Advanced synthesis & catalysis			2010	777	0

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Cheng, Xin