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

作者：Anh Ngoc Ngo; El Kassimi Khadija; Amara Zacharias; Drege Emmanuelle^*; Joseph Delphine

来源：Tetrahedron Letters, 2012, 53(26): 3296-3300.

DOI：10.1016/j.tetlet.2012.04.069

• Michael reaction
• Cyclization
• Organocatalysis
• Chiral auxiliaries

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.

• 出版日期2012-6-27