Dramatic Solvent Effect on the Diastereoselectivity of Michael Addition: Study toward the Synthesis of the ABC Ring System of Hexacyclinic Acid

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• 作者：Julie Toueg ; Jo&euml ; lle Prunet
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：January 3, 2008
• 年：2008
• 卷：10
• 期：1
• 页码：45 - 48
• 全文大小：107K
• 年卷期：v.10,no.1(January 3, 2008)
• ISSN：1523-7052

文摘

During our studies toward the synthesis of the ABC ring system of hexacyclinic acid, we have observed a dramatic influence of the solventon both our key steps. The diastereoselectivity of the intermolecular Michael addition could be totally reversed by changing the polarity of thesolvent, and trifluoroethanol was found to be the optimal solvent for the following Mn(III)-promoted radical cyclization.