Amine-mediated tandem conjugative isomerization-bridging Michael addition: Concise synthesis of 1-azabicyclo[3.3.1]nonanes
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.
Ngo, Anh Ngoc,El Kassimi, Khadija,Amara, Zacharias,Drège, Emmanuelle,Joseph, Delphine
scheme or table
p. 3296 - 3300
(2012/08/08)
A One-pot Synthesis of (E)-5-Bromo-2-pentenoate Esters
Addition of hydrogen bromide gas to acrolein followed by reaction with a stabilized triphenylphosphoranylidene ylide in benzene solvent affords (E)-5-bromo-2-pentenoate esters in 60-80percent yield with greater than 90percent selectivity for the E double bond isomer.
Bunce, Richard A.,Irwin, Derek A.
p. 2979 - 2982
(2007/10/02)
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