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Further studies on vinamidinium salt amine exchange reactions, borohydride reductions and subsequent transformations
Authors:Gupton John T  Telang Nakul  Jia Xin  Giglio Benjamin C  Eaton James E  Barelli Peter J  Hovaizi Mona  Hall Kayleigh E  Welden R Scott  Keough Matthew J  Worrall Eric F  Finzel Kara L  Kluball Emily J  Kanters Rene P F  Smith Timothy M  Smith Stanton Q  Nunes Shane R  Wright Mathew T  Birnstihl Jennifer M
Institution:a Department of Chemistry, University of Richmond, Richmond, VA 23173, USA
b Department of Chemistry, Virginia Military Institute, Lexington, VA 24450, USA
c Department of Chemistry, University of Central Florida, Orlando, FL 32816, USA
Abstract:Studies directed at the amine exchange reaction of vinamidinium salts followed by sodium borohydride reduction to secondary and tertiary allylic amines are described. The tertiary allylic amines were alkylated and subjected to base mediated rearrangement to yield a variety of highly functionalized tertiary homoallylic amines.
Keywords:Vinamidinium salt  Allylic amine  Reduction  2  3-Sigmatropic rearrangement
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