Determination of the absolute configuration of optically active 2,2-dimethyl-3,4-epoxychromans prepared by the catalytic enantioselective epoxidation with the dimethyldioxirane/Jacobsen Mn(III)salen system

Waldemar Adam, József Jeko, Albert Lévai, Zsuzsa Majer, Csaba Nemes, Tamás Patonay, László Párkányi, Péter Sebok

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15 Citations (Scopus)

Abstract

Enantioselective epoxidation of 2,2-dimethyl-2H-chromenes 1a-d by using Mn(III)salen complexes (R,R)-3 and (S,S)-3 as catalysts and dimethyldioxirane (DMD) as oxygen donor afforded optically active 2,2-dimethyl-3,4-epoxychromans 2a-d in good yields and high enantioselectivities (up to 93% e.e.). The absolute configuration of the (3S,4S)-6,7-bis(tosyloxy)-2,2-dimethyl-3,4-epoxychroman (3S,4S)-2d has been determined by X-ray diffraction. The absolute configurations of the other nonracemic epoxychromas were assigned by circular dichroism (CD) measurements relative to the (3S,4S)-2d epoxide as reference compound.

Original languageEnglish
Pages (from-to)2437-2446
Number of pages10
JournalTetrahedron Asymmetry
Volume7
Issue number8
DOIs
Publication statusPublished - Aug 1996

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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