Synthesis of Bicyclic Tertiary -Amino Acids

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• 作者：Jon-Paul Strachan ; Regina C. Whitaker ; Craig H. Miller ; Balwinder S. Bhatti
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：December 22, 2006
• 年：2006
• 卷：71
• 期：26
• 页码：9909 - 9911
• 全文大小：66K
• 年卷期：v.71,no.26(December 22, 2006)
• ISSN：1520-6904

文摘

Novel bicyclic -amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generationof neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic etherelectrophiles, followed by acid-induced ring opening andcyclization in NH₄OH, allowed for the preparation ofsubstantial quantities of the three tertiary bicyclic -aminoacids.