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

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 t...

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Bibliographic Details
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:	Kidlington Elsevier Ltd 30-10-2010 Elsevier
Subjects:	2,3-Sigmatropic rearrangement Alkylation Allylic amine Amines Borohydrides Chemistry Exact sciences and technology Exchange Kinetics and mechanisms Organic chemistry Reactivity and mechanisms Reduction Sodium Tetrahedrons Transformations Vinamidinium salt 2,3-Sigmatropic rearrangement Allylic amine Reduction NRQKZOXFWLKDHO-UHFFFAOYSA-N JDEQPRNCPXXHTB-UHFFFAOYSA-N Vinamidinium salt GESAJPPZBOSQBU-UHFFFAOYSA-N Sigmatropic reaction Chemical rearrangement Organic cation Iminium compounds Exchange reaction Sodium Tetrahydroborates Alkylation Allylic compound Chemical reduction Functionalization Tertiary amine Secondary amine Homoallylic compound
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Summary:	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]
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2010.08.075