Further studies of intramolecular Michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems |
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Authors: | Kumar Praveen Li Puhui Korboukh Ilia Wang Tony L Yennawar Hemant Weinreb Steven M |
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Institution: | Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. |
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Abstract: | 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-azabicyclo3.2.1]octane. |
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