Highly enantioselective synthesis of chiral secondary amines by gold(I)/chiral Brønsted acid catalyzed tandem intermolecular hydroamination and transfer hydrogenation reactions

Xin-Yuan Liu; Chi-Ming Che

doi:10.1021/ol901443b

Highly enantioselective synthesis of chiral secondary amines by gold(I)/chiral Brønsted acid catalyzed tandem intermolecular hydroamination and transfer hydrogenation reactions

Org Lett. 2009 Sep 17;11(18):4204-7. doi: 10.1021/ol901443b.

Authors

Xin-Yuan Liu¹, Chi-Ming Che

Affiliation

¹ Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, PR China.

PMID: 19678678
DOI: 10.1021/ol901443b

Abstract

A method for the synthesis of enantiomerically enriched secondary amines with excellent ee values through the tandem intermolecular hydroamination/transfer hydrogenation of alkynes using a "gold(I) complex-chiral Brønsted acid" protocol is developed. The catalysis works for a wide variety of aryl, alkenyl, and aliphatic alkynes as well as anilines with different electronic properties.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry
Amines / chemical synthesis*
Aniline Compounds / chemistry
Catalysis
Cyclization
Gold / chemistry*
Hydrogenation
Molecular Structure
Stereoisomerism

Substances

Alkynes
Amines
Aniline Compounds
Gold
aniline