Further studies on vinamidinium salt amine exchange reactions, borohydride reductions, and subsequent transformations

• Published in: Tetrahedron Vol. 66; no. 44; pp. 8485 - 8493
• Main 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.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.10.2010; Elsevier
• Subjects: 2,3-Sigmatropic rearrangement; Alkylation; Allylic amine; Amines; Borohydrides; Chemistry; Chemistry, Organic; Exact sciences and technology; Exchange; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Reduction; Science & Technology; Sodium; Tetrahedrons; Transformations; Vinamidinium salt; 2,3-Sigmatropic rearrangement; Allylic amine; Reduction; NRQKZOXFWLKDHO-UHFFFAOYSA-N; JDEQPRNCPXXHTB-UHFFFAOYSA-N; Vinamidinium salt; GESAJPPZBOSQBU-UHFFFAOYSA-N; QUATERNARY AMMONIUM-SALTS; 2-ARYL-3-(N,N-DIMETHYLAMINO)-1-PROPENES; Sigmatropic reaction; Chemical rearrangement; Organic cation; Iminium compounds; Exchange reaction; Sodium Tetrahydroborates; Alkylation; Allylic compound; Chemical reduction; Functionalization; Tertiary amine; Secondary amine; Homoallylic compound
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.08.075

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. [Display omitted]