Role of the Countercation in Diastereoselective Alkylations of Pyramidalized Bicyclic Serine Enolates. An Easy Approach to -Benzylse

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• 作者：Gonzalo Jimé ; nez-Osé ; s ; Carlos Aydillo ; Jes&uacute ; s H. Busto ; Marí ; a M. Zurbano ; Jes&uacute ; s M. Peregrina ; Alberto Avenoza
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：July 6, 2007
• 年：2007
• 卷：72
• 期：14
• 页码：5399 - 5402
• 全文大小：147K
• 年卷期：v.72,no.14(July 6, 2007)
• ISSN：1520-6904

文摘

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The use of a chiral serine equivalent as an excellent chiralbuilding block has been demonstrated in the synthesis ofmages/gifchars/alpha.gif" BORDER=0>-benzylserine through a diastereoselective lithium enolatealkylation reaction and subsequent acid hydrolysis. The roleof a coordinating countercation (lithium) in the alkylationreaction has been investigated. Theoretical studies have beenperformed in order to elucidate the stereochemical outcomeof the alkylation process, which occurs with total retentionof configuration.