trans-Hydroboration of Propiolamides: Access to Primary and Secondary (E)-β-Borylacrylamides
R. Justin Grams, Russell G. Fritzemeier, Carla Slebodnick, Webster L. Santos*
*Department of Chemistry, Virginia Tech, 900 West Campus Drive, Blacksburg, Virginia 24061, United States, Email: santoswvt.edu
R. J. Grams, R. G. Fritzemeier, C. Slebodnick, W. L. Santos, Org. Lett., 2019, 21, 6795-6799.
DOI: 10.1021/acs.orglett.9b02408 (free Supporting Information)
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A base-mediated trans-hydroboration of a wide range of propiolamides provides access to previously elusive primary and secondary (E)-β-borylacrylamides. The use of n-butyllithium and pinacolborane provides the corresponding vinylboronates in very good yields with complete regioselectivity and stereoselectivity.
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