Nickel/Brønsted Acid-Catalyzed Chemo- and Enantioselective Intermolecular Hydroamination of Conjugated Dienes

A novel nickel/Brønsted acid-catalyzed asymmetric hydroamination of acyclic 1,3-dienes has been established. A wide array of primary and secondary amines can be transformed into allylic amines with high yields and high enantioselectivities under very mild conditions. Moreover, our method is compatib...

Full description

Saved in:
Bibliographic Details
Published iniScience Vol. 22; pp. 369 - 379
Main Authors Long, Jiao, Wang, Peng, Wang, Wang, Li, Yuqiang, Yin, Guoyin
Format Journal Article
LanguageEnglish
Published United States Elsevier Inc 20.12.2019
Elsevier
Subjects
Catalysis
Materials Chemistry
Organic Synthesis
Materials Chemistry
Organic Synthesis
Catalysis
Online AccessGet full text

Cover

More Information
Summary:A novel nickel/Brønsted acid-catalyzed asymmetric hydroamination of acyclic 1,3-dienes has been established. A wide array of primary and secondary amines can be transformed into allylic amines with high yields and high enantioselectivities under very mild conditions. Moreover, our method is compatible with various functional groups and heterocycles, allowing for late-stage functionalization of biologically active complex molecules. Remarkably, this protocol exhibits good chemoselectivity with respect to amines bearing two different nucleophilic sites. Mechanistic studies reveal that the enantioselective carbon-nitrogen bond-forming step is reversible. [Display omitted] •Nickel/Brønsted acid-catalyzed asymmetric hydroamination of conjugated dienes•High regio-, chemo-, and enantioselectivity•Broad range of substrate scope•Wide functional group tolerance Catalysis; Organic Synthesis; Materials Chemistry
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Lead Contact
ISSN:2589-0042
2589-0042
DOI:10.1016/j.isci.2019.11.008