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, J. Jekó́, A. Lévai, Zs. Majer, Csaba Nemes, T. Patonay, L. Párkányí, Péter Sebok

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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

Fingerprint

epoxidation
Epoxidation
Enantioselectivity
Epoxy Compounds
Dichroism
Circular Dichroism
X-Ray Diffraction
Oxygen
X ray diffraction
Catalysts
epoxy compounds
configurations
dichroism
catalysts
oxygen
diffraction
x rays
disalicylaldehyde ethylenediamine
dimethyldioxirane
5,7-dimethoxy-2-methyl-2H-benzopyran

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

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title = "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",
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.",
author = "Waldemar Adam and J. Jek{\'o}́ and A. L{\'e}vai and Zs. Majer and Csaba Nemes and T. Patonay and L. P{\'a}rk{\'a}ny{\'i} and P{\'e}ter Sebok",
year = "1996",
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T1 - 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

AU - Adam, Waldemar

AU - Jekó́, J.

AU - Lévai, A.

AU - Majer, Zs.

AU - Nemes, Csaba

AU - Patonay, T.

AU - Párkányí, L.

AU - Sebok, Péter

PY - 1996/8

Y1 - 1996/8

N2 - 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.

AB - 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.

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