1272489-16-3Relevant academic research and scientific papers
Further studies of intramolecular michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems
Kumar, Praveen,Li, Puhui,Korboukh, Ilia,Wang, Tony L.,Yennawar, Hemant,Weinreb, Steven M.
, p. 2094 - 2101 (2011/06/17)
A wide variety of stabilized carbanions have been found to participate as nucleophiles in intramolecular Michael-type conjugate additions to in situ generated nitrosoalkenes to form bridged carbocyclic systems. The vinylnitroso platforms for these cyclizations have been prepared via two key steps involving ring-closing metathesis of vinyl chlorides and regioselective conversion of vinyl chlorides to α-chloroketones with sodium hypochlorite in glacial acetic acid/acetone. An alternative approach to preparation of some cyclization substrates has involved use of more reactive enol ethers as precursors to the requisite α-chloroketones. A sulfonamide anion has also been found to be an effective nucleophile in this type of reaction, leading to formation of a 6-azabicyclo[3.2.1]octane.
