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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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Abstract

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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Key Words

vinylboronates


ID: J54-Y2019