The Mitsunobu inversion reaction of sterically hindered 17-hydroxy steroids

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13 Citations (Scopus)

Abstract

The Mitsunobu inversion reaction of 3-methoxyestra-1,3,5(10)-trien- 17β-ol is dramatically influenced by the acidic component. There appears to be a relationship between the dissociation constant of the electron-withdrawing substituent on the aryl acid and the overall effectiveness of the reaction, with more acidic species generally providing a higher yield of inverted product.

Original languageEnglish
Pages (from-to)1129-1136
Number of pages8
JournalMonatshefte fur Chemie
Volume135
Issue number9
DOIs
Publication statusPublished - Sep 2004

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Trientine
Steroids
Acids
Electrons

Keywords

  • Carboxylic acids
  • Estrone derivatives
  • Isomers
  • Mitsunobu reaction
  • Steroids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "The Mitsunobu inversion reaction of 3-methoxyestra-1,3,5(10)-trien- 17β-ol is dramatically influenced by the acidic component. There appears to be a relationship between the dissociation constant of the electron-withdrawing substituent on the aryl acid and the overall effectiveness of the reaction, with more acidic species generally providing a higher yield of inverted product.",
keywords = "Carboxylic acids, Estrone derivatives, Isomers, Mitsunobu reaction, Steroids",
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AU - Wölfling, J.

AU - Mernyák, E.

AU - Schneider, G.

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AB - The Mitsunobu inversion reaction of 3-methoxyestra-1,3,5(10)-trien- 17β-ol is dramatically influenced by the acidic component. There appears to be a relationship between the dissociation constant of the electron-withdrawing substituent on the aryl acid and the overall effectiveness of the reaction, with more acidic species generally providing a higher yield of inverted product.

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KW - Estrone derivatives

KW - Isomers

KW - Mitsunobu reaction

KW - Steroids

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JF - Monatshefte fur Chemie

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