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

Von Oppolzer, Wolfgang; Rodriguez, Ines

doi:10.1002/hlca.19930760315

Scientific article

English

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

ContributorsVon Oppolzer, Wolfgang; Rodriguez, Ines

Published inHelvetica chimica acta, vol. 76, no. 3, p. 1282-1291

Publication date1993

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.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON 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. doi: 10.1002/hlca.19930760315

Article (Published version)

Identifiers

PID : unige:85274
DOI : 10.1002/hlca.19930760315

Journal ISSN0018-019X

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

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