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

Tamás Patonay, József Jeko, Attila Kiss-Szikszai, Albert 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 1 2004

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

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