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Stereoselective vinylation of aryl N-(2-pyridylsulfonyl) aldimines with 1-alkenyl-1,1-heterobimetallic reagents
Authors:Hussain Nusrah  Hussain Mahmud M  Ziauddin Muhammed  Triyawatanyu Plengchat  Walsh Patrick J
Institution:P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Abstract:Vinylation of aryl N-(2-pyridylsulfonyl) aldimines with versatile 1-alkenyl-1,1-borozinc heterobimetallic reagents is disclosed. In situ hydroboration of air-stable B(pin)-alkynes followed by chemoselective transmetalation with dimethylzinc and addition to aldimines provides B(pin)-substituted allylic amines in 53-93% yield in a one-pot procedure. The addition step can be followed by either B-C bond oxidation to provide α-amino ketones (71-98% yield) or Suzuki cross-coupling to furnish trisubstituted 2-arylated (E)-allylic amines (51-73% yield).
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