Ru-TsDPEN with Formic Acid/Hünig's Base for Asymmetric Transfer Hydrogenation, a Practical Synthesis of Optically Enriched N-Propyl Pantolactam

The Noyori-Ikariya catalysts, Ru-TsDPEN 1 or 2, in combination with HCOOH/Hunig's base (5:2) have been successfully utilized for catalytic asymmetric transfer hydrogenation of alpha-ketopantolactam, and optically enriched N-substituted pantolactam was prepared (S/C = 500, up to 95% ee and 99% c...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2009-02, Vol.74 (3), p.1411-1414
Main Authors: JI ZHANG, BLAZECKA, Peter G, BRUENDL, Michelle M, YUN HUANG
Format: Article
Language:English
Subjects:
Amines - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Ethylenediamines - chemistry
Exact sciences and technology
Formates - chemistry
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrogenation
Lactams - chemical synthesis
Organic chemistry
Organometallic Compounds - chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The Noyori-Ikariya catalysts, Ru-TsDPEN 1 or 2, in combination with HCOOH/Hunig's base (5:2) have been successfully utilized for catalytic asymmetric transfer hydrogenation of alpha-ketopantolactam, and optically enriched N-substituted pantolactam was prepared (S/C = 500, up to 95% ee and 99% conversion in HCOOH/Hunig's base condition). More than 2 kg of this key intermediate 9 has been synthesized efficiently with excellent chemical yield and chiral purity.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802380j