Development and application of a direct vinyl lithiation of cis-stilbene and a directed vinyl lithiation of an unsymmetrical cis-stilbene |
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Authors: | Cotter Juliet Hogan Anne-Marie L O'Shea Donal F |
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Institution: | Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland. |
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Abstract: | reaction: see text] The vinyl deprotonation of cis-stilbene can be readily achieved using s-BuLi in THF at -25 degrees C. The generated 1-lithio-1,2-diphenylethene undergoes an in situ Z-to-E isomerization, and subsequent reaction with electrophiles results in an efficient stereoselective synthesis of trisubstituted alkenes. A directed vinyl lithiation of the unsymmetrical cis-stilbene 2-styryl-phenyl-carbamic acid tert-butyl ester can be achieved regioselectively, thereby expanding this methodology for further synthetic applications in indole chemistry. |
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