Tetrahedron Letters

Amine-mediated tandem conjugative isomerization-bridging Michael addition: concise synthesis of 1-azabicyclo [3.3. 1] nonanes

AN Ngo, K El Kassimi, Z Amara, E Drège, D Joseph

Index: Ngo, Anh Ngoc; El Kassimi, Khadija; Amara, Zacharias; Drege, Emmanuelle; Joseph, Delphine Tetrahedron Letters, 2012 , vol. 53, # 26 p. 3296 - 3300

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Citation Number: 2

Abstract

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.