Efficient enantioselective synthesis of 3-aminochroman derivatives through ruthenium-Synphos catalyzed asymmetric hydrogenation

Zi Wu; Tahar Ayad; Virginie Ratovelomanana-Vidal

doi:10.1021/ol201786q

Efficient enantioselective synthesis of 3-aminochroman derivatives through ruthenium-Synphos catalyzed asymmetric hydrogenation

Org Lett. 2011 Aug 5;13(15):3782-5. doi: 10.1021/ol201786q. Epub 2011 Jul 14.

Authors

Zi Wu¹, Tahar Ayad, Virginie Ratovelomanana-Vidal

Affiliation

¹ Chimie ParisTech, Laboratoire Charles Friedel (LCF), 75005 Paris, France,.

PMID: 21755918
DOI: 10.1021/ol201786q

Abstract

A highly enantioselective asymmetric hydrogenation of various trisubstituted enamides derived from chroman-3-ones promoted by cationic Ru-Synphos catalysts is reported. This atom-economical and clean method provides an efficient route to optically active 3-aminochroman derivatives, which are important pharmacophores found in numerous drug candidates, in high chemical yields and enantiomeric excesses up to 96%.

Publication types

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

MeSH terms

Catalysis
Chromans / chemical synthesis*
Hydrogenation
Molecular Structure
Ruthenium / chemistry*
Stereoisomerism

Substances

3-aminochroman
Chromans
Ruthenium