title: Stereoselective vinylation of aryl N-(2-pyridylsulfonyl) aldimines with 1-alkenyl-1,1-heterobimetallic reagents.
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).
authors.affiliation: P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Nusrah
authors.initials: N
authors.lastname: Hussain
authors.forename: Mahmud M
authors.initials: MM
authors.lastname: Hussain
authors.forename: Muhammed
authors.initials: M
authors.lastname: Ziauddin
authors.forename: Plengchat
authors.initials: P
authors.lastname: Triyawatanyu
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry
chemical_list: D000475:Alkenes; D000480:Alkynes; D007097:Imines; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D011725:Pyridines; D013450:Sulfones; D015032:Zinc
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