Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2015 Sep 9;137(35):11246-9.
doi: 10.1021/jacs.5b07203. Epub 2015 Aug 27.

Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives

Derick R White  1 , Johnathon T Hutt  1 , John P Wolfe  1
Affiliations

Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives

Derick R White et al. J Am Chem Soc. .

Abstract

A new type of Pd-catalyzed alkene carboamination reaction that provides direct access to enantioenriched 2-aminoindanes from 2-allylphenyltriflate derivatives and aliphatic amines is described. A catalyst generated in situ from Pd(OAc)2 and (S)-tert-butylPHOX provides the functionalized carbocycles in good yield with up to >99:1 er. The transformations occur via a key anti-aminopalladation that involves intermolecular attack of an amine nucleophile on an arylpalladium alkene complex.

PubMed Disclaimer

Conflict of interest statement

Notes

The authors declare no competing financial interests.

Figures

Scheme 1
Scheme 1
anti-Aminopalladation Mechanisms
Scheme 2
Scheme 2
Stereochemical Model
See this image and copyright information in PMC

References

    1. For reviews on Pd-catalyzed alkene carboamination reactions for the synthesis of nitrogen heterocycles, see:

    2. Schultz DM, Wolfe JP. Synthesis. 2012;44:351. - PMC - PubMed
    3. Wolfe JP. Top Heterocycl Chem. 2013;32:1–38.
    1. Mai DN, Wolfe JP. J Am Chem Soc. 2010;132:12157. - PMC - PubMed
    1. Hopkins BA, Wolfe JP. Angew Chem Int Ed. 2012;51:9886. - PMC - PubMed
    1. Hopkins BA, Wolfe JP. Chem Sci. 2014;5:4840. - PMC - PubMed
    1. Fornwald RM, Fritz JA, Wolfe JP. Chem Eur J. 2014;20:8782. - PMC - PubMed

Publication types

LinkOut - more resources