Enantio- and Regioselective CuH-Catalyzed Hydroamination of Alkenes

A highly enantio- and regioselective copper-catalyzed hydroamination reaction of alkenes has been developed using diethoxymethylsilane and esters of hydroxylamines. The process tolerates a wide variety of substituted styrenes, including trans-, cis-, and β,β-disubstituted styrenes, to yield α-branch...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2013-10, Vol.135 (42), p.15746-15749
Main Authors: Zhu, Shaolin, Niljianskul, Nootaree, Buchwald, Stephen L
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Amination
Amines - chemical synthesis
Amines - chemistry
Catalysis
Copper - chemistry
Hydrogen - chemistry
Molecular Structure
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A highly enantio- and regioselective copper-catalyzed hydroamination reaction of alkenes has been developed using diethoxymethylsilane and esters of hydroxylamines. The process tolerates a wide variety of substituted styrenes, including trans-, cis-, and β,β-disubstituted styrenes, to yield α-branched amines. In addition, aliphatic alkenes coupled to generate exclusively the anti-Markovnikov hydroamination products.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja4092819