The Mitsunobu Inversion Reaction of Sterically Hindered 17-Hydroxy Steroids |
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| Authors: | Pál Tapolcsányi János Wélfling Erzs?bet Mernyák Gyula Schneider |
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| Affiliation: | (1) Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 16610 Prague 6, Czech Republic;(2) Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12843 Praha 2, Czech Republic;(3) Laboratory of Experimental Medicine, Departments of Pediatrics and Oncology, Faculty of Medicine, Palacky University in Olomouc, Puskinova 6, 77520 Olomouc, Czech Republic;(4) Department of Organic Chemistry, Faculty of Science, Palacky University in Olomouc, Trida Svobody 8, 77200 Olomouc, Czech Republic; |
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| Abstract: | The Mitsunobu inversion reaction of 3-methoxyestra-1,3,5(10)-trien-17 -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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