Amine-mediated tandem conjugative isomerization-bridging Michael addition: concise synthesis of 1-azabicyclo[3.3.1]nonanes

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• 作者：Anh Ngoc Ngo ; Khadija El Kassimi ; Zacharias Amara ; Emmanuelle Drè ; ge ; Delphine Joseph ; ^{delphine.joseph@u-psud.fr}
• 关键词：Michael reaction ; Cyclization ; Organocatalysis ; Chiral auxiliaries
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：27 June, 2012
• 年：2012
• 卷：53
• 期：26
• 页码：3296-3300
• 全文大小：741 K

文摘

To reach densely functionalized 1-azabicyclo[3.3.1]nonane frameworks synthesis, a stereocontrolled bridging Michael addition involving an unexplored C-5/C-6 disconnection strategy was studied. 1-Azabicyclo[3.3.1]nonane scaffolds have been diastereoselectively elaborated in fairly good yields by two concise pathways implying pyrrolidine derivative organocatalyst or enantiopure 1-phenylethylamine.