Rhodium-Catalyzed Asymmetric Hydrogenation of N-(1-benzylpiperidin-3-yl)-enamides: An Efficient Access to Valuable Enantioenriched 3-Aminopiperidine Derivatives

Abstract An efficient synthetic entry to enantioenriched 3-aminopiperidine derivatives using rhodium-catalyzed asymmetric hydrogenation of N -(1-benzylpiperidin-3-yl)enamides is described. This method provides an atom-economical and attractive route to both enantiomers of the valuable 3-aminopiperid...

Full description

Saved in:
Bibliographic Details
Published in:Synlett 2016-08, Vol.27 (13), p.2009-2013
Main Authors: Royal, Titouan, Dudognon, Yohan, Berhal, Farouk, Bastard, Yvon, Boudet, Bernard, Ayad, Tahar, Ratovelomanana-Vidal, Virginie
Format: Article
Language:English
Subjects:
letter
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract An efficient synthetic entry to enantioenriched 3-aminopiperidine derivatives using rhodium-catalyzed asymmetric hydrogenation of N -(1-benzylpiperidin-3-yl)enamides is described. This method provides an atom-economical and attractive route to both enantiomers of the valuable 3-aminopiperidine moiety, which is an important structural unit that can be found in many natural products and pharmaceutical drugs encompassing a broad range of biological activities. Under optimized reaction conditions, the targeted 3-aminopiperidine derivatives were obtained in high yields up to 92% and with enantiomeric excesses up to 96% after a single crystallization.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0035-1562235