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Stereocontrolled Syntheses of Polysubstituted 2,3-Dihydro-4H-pyran-4-ones by cyclocondensation of β-acyloxy-ketones

Authors
Oppolzer, Wolfgang
Published in Helvetica Chimica Acta. 1993, vol. 76, no. 3, p. 1282-1291
Abstract syn-β-Acyloxy-ketones 6 and an anti-β-acyloxy-ketone 17 undergo smooth intramolecular enolate/ester condensations 6 [RIGHTWARDS ARROW] 18 and 17 [RIGHTWARDS ARROW] 19 when treated with TiCl4/EtN(i-Pr)2. Thus, tri- and tetrasubstituted cis- or trans-2,3-dihydro-4H-pyran-4-ones are easily prepared in a stereoselective manner.
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Other version: http://doi.wiley.com/10.1002/hlca.19930760315
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OPPOLZER, Wolfgang, RODRIGUEZ, Ines. Stereocontrolled Syntheses of Polysubstituted 2,3-Dihydro-4H-pyran-4-ones by cyclocondensation of β-acyloxy-ketones. In: Helvetica Chimica Acta, 1993, vol. 76, n° 3, p. 1282-1291. https://archive-ouverte.unige.ch/unige:85274

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