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Tantalum Catalyzed Hydroaminoalkylation for the Synthesis of alpha- and beta-Substituted N-Heterocycles

TitleTantalum Catalyzed Hydroaminoalkylation for the Synthesis of alpha- and beta-Substituted N-Heterocycles
Publication TypeJournal Article
Year of Publication2013
AuthorsPayne, PR, Garcia, P, Eisenberger, P, Yim, JC-H, Schafer, LL
JournalOrganic Letters
Volume15
Pagination2182-2185
Date PublishedMAY 3
ISSN1523-7060
Abstract

Unprotected secondary amines are directly alkylated by C-H functionalization adjacent to nitrogen, thereby opening new routes toward the synthesis of alpha- and beta-alkylated N-heterocycles. alpha-Alkylated piperidine, piperazine, and azepane products are prepared from heterocycles and alkenes in an atom-economic reaction with excellent regio- and diastereoselectivity. beta-Alkylated N-heterocycles are synthesized via a scalable one-pot alkylation/cyclization procedure generating 3-methylated azetidines, pyrrolidines, and piperidines.

DOI10.1021/ol400729v