Synthesis of racemic and enantiomerically enriched α- oxyfunctionalized benzocyclanones and chromanones by dimethyldioxirane and dimethyldioxirane/Mn(III) salen system

T. Patonay, J. Jekó́, Attila Kiss-Szikszai, A. Lévai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic α-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position α in the whole series.

Original languageEnglish
Pages (from-to)743-756
Number of pages14
JournalMonatshefte fur Chemie
Volume135
Issue number6
DOIs
Publication statusPublished - Jun 2004

Fingerprint

Tetralones
Enantioselectivity
Ketones
Acetates
Ligands
Catalysts
disalicylaldehyde ethylenediamine
dimethyldioxirane
flavanone

Keywords

  • Dioxirane
  • Enantioselective epoxidation
  • Enolacetates
  • Jacobsen-Katsuki's catalyst

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Synthesis of racemic and enantiomerically enriched α- oxyfunctionalized benzocyclanones and chromanones by dimethyldioxirane and dimethyldioxirane/Mn(III) salen system",
abstract = "Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic α-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position α in the whole series.",
keywords = "Dioxirane, Enantioselective epoxidation, Enolacetates, Jacobsen-Katsuki's catalyst",
author = "T. Patonay and J. Jek{\'o}́ and Attila Kiss-Szikszai and A. L{\'e}vai",
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T1 - Synthesis of racemic and enantiomerically enriched α- oxyfunctionalized benzocyclanones and chromanones by dimethyldioxirane and dimethyldioxirane/Mn(III) salen system

AU - Patonay, T.

AU - Jekó́, J.

AU - Kiss-Szikszai, Attila

AU - Lévai, A.

PY - 2004/6

Y1 - 2004/6

N2 - Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic α-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position α in the whole series.

AB - Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic α-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position α in the whole series.

KW - Dioxirane

KW - Enantioselective epoxidation

KW - Enolacetates

KW - Jacobsen-Katsuki's catalyst

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