Tantalum Catalyzed Hydroaminoalkylation for the Synthesis of α- and β‑Substituted N‑Heterocycles

Unprotected secondary amines are directly alkylated by C–H functionalization adjacent to nitrogen, thereby opening new routes toward the synthesis of α- and β-alkylated N-heterocycles. α-Alkylated piperidine, piperazine, and azepane products are prepared from heterocycles and alkenes in an atom-econ...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 15; no. 9; pp. 2182 - 2185
Main Authors Payne, Philippa R, Garcia, Pierre, Eisenberger, Patrick, Yim, Jacky C.-H, Schafer, Laurel L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.05.2013
Amer Chemical Soc
Subjects
Alkylation
Azetidines - chemical synthesis
Azetidines - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Physical Sciences
Piperidines - chemical synthesis
Piperidines - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Science & Technology
Stereoisomerism
Tantalum - chemistry
FUNCTIONALIZATION
ALKENES
AMINES
NITROGEN ATOM
ARYLATION
BOND ACTIVATION
UNACTIVATED OLEFINS
ADJACENT
C-H ACTIVATION
DERIVATIVES
Online AccessGet full text

Cover

More Information
Summary:Unprotected secondary amines are directly alkylated by C–H functionalization adjacent to nitrogen, thereby opening new routes toward the synthesis of α- and β-alkylated N-heterocycles. α-Alkylated piperidine, piperazine, and azepane products are prepared from heterocycles and alkenes in an atom-economic reaction with excellent regio- and diastereoselectivity. β-Alkylated N-heterocycles are synthesized via a scalable one-pot alkylation/cyclization procedure generating 3-methylated azetidines, pyrrolidines, and piperidines.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400729v